Phenylsulfonyl ureas, process for their preparation and their use as herbicides and plant growth regulators

ABSTRACT

Compounds of the formula (I) or salts thereof  
                 
in which 
     R 1  is a hydrogen atom, a hydrocarbon radical or a heterocyclyl radical, where each of the two last-mentioned radicals is unsubstituted or substituted and, including substituents, has from 1 to 30 carbon atoms, preferably from 1 to 20 carbon atoms,    R 2  is a group of the formula R 0 -Q 0 - in which 
       R 0  is a hydrogen atom, a hydrocarbon radical or a heterocyclyl radical, where each of the two last-mentioned radicals is unsubstituted or substituted and, including substituents, has from 1 to 30 carbon atoms, preferably from 1 to 20 carbon atoms, and    Q is a direct bond or a divalent group of the formula —O— or —N(R # )—, where R #  is a hydrogen atom, an acyl radical or a hydrocarbon radical and where the last-mentioned radical is unsubstituted or substituted and, including substituents, has from 1 to 30 carbon atoms, preferably from 1 to 20 carbon atoms,    
       R 3  is a hydrogen atom, a hydrocarbon radical or a heterocyclyl radical, where each of the two last-mentioned radicals is unsubstituted or substituted and, including substituents, has from 1 to 30 carbon atoms, preferably from 1 to 20 carbon atoms,    R 4  independently of one another, are halogen, OH, SH, a nitrogen-containing radical which does not contain any carbon or a carbon-containing radical, is 0, 1, 2 or 3, preferably 0 or 1,    R 5  is a hydrogen atom or a C 1 -C 10 -hydrocarbon radical which is unsubstituted or substituted, such as (C 1 -C 4 )alkyl, preferably H or CH 3 ), Q is O, S or NR*,    R* is a hydrogen atom or a C 1 -C 10 -hydrocarbon radical which is unsubstituted or substituted such as (C 1 -C 4 )alkyl, (C 3 -C 4 )alkenyl or (C 3 -C 4 )alkynyl, where each of the three last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylthio, W is an oxygen or sulfur atom,    X,Y independently of one another are a hydrogen atom, halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkylthio, where each of the 3 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C 1 -C 4 )alkoxy and (C 1 -C 4 )alkylthio, or are mono- or di[(C 1 -C 4 )alkyl]amino, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 3 -C 6 )alkenyloxy or (C 3 -C 6 )alkynyloxy, and V, Z independently of one another are CH or N, 
 
are suitable for use as herbicides or plant growth regulators, for example for controlling harmful plants in crop plants, including transgenic crop plants. They can be prepared by the processes according to claim  6  via intermediates, some of which are novel (cf. compounds (II*) and (X*) and (VIII) as claimed in claims  12, 14  and  16).

It is known that substituted phenylsulfonyl ureas have herbicidalproperties. These are benzoic acid derivatives of the general formula A(EP-A-7 687 and EP-A-30 138).

Furthermore, DEA 322.067 discloses that acylamino-substitutedphenylsulfonyl ureas have herbicidal properties.

Surprisingly, specific 1,2,3-substituted phenylsulfonyl ureas have nowbeen found which are particularly suitable for use as herbicides orplant growth regulators.

Accordingly, the present invention provides compounds of the formula,(I) or salts thereof

in which

-   R¹ is a hydrogen atom, a hydrocarbon radical or a heterocyclyl    radical, where each of the two last-mentioned radicals is    unsubstituted or substituted and, including substituents, has from 1    to 30 carbon atoms, preferably from 1 to 20 carbon atoms,-   R² is a group of the formula R⁰-Q⁰- in which    -   R⁰ is a hydrogen atom, a hydrocarbon radical or a heterocyclyl        radical, where each of the two last-mentioned radicals is        unsubstituted or substituted and, including substituents, has        from 1 to 30, carbon atoms, preferably from 1 to 20 carbon        atoms, and    -   Q⁰ is a direct bond or a divalent group of the formula —O— or        —N(R^(#))—, where R^(#) is a hydrogen atom, an acyl radical or a        hydrocarbon radical and where the last-mentioned radical is        unsubstituted or substituted and, including substituents, has        from 1 to 30 carbon atoms, preferably from 1 to 20 carbon atoms,-   R³ is a hydrogen atom, a hydrocarbon radical or a heterocyclyl    radical, where each of the two last-mentioned radicals is    unsubstituted or substituted and, including substituents, has from 1    to 30 carbon atoms, preferably from 1 to 20 carbon atoms,-   R⁴ independently of one another, are halogen, OH, SH, a    nitrogen-containing radical which does not contain any carbon or a    carbon-containing radical which has from 1 to 30 carbon atoms,    preferably from 1 to 20 carbon atoms, is 0, 1, 2 or 3, preferably 0    or 1,-   R⁵ is a hydrogen atom or a hydrocarbon radical which is    unsubstituted or substituted and, including substituents, has from 1    to 20 carbon atoms, preferably from 1 to 10 carbon atoms, for    example unsubstituted or substituted (C₁-C₄)alkyl, preferably H or    CH₃,-   Q is O, S or NR*,-   R* is a hydrogen atom or a C₁-C₁₀-hydrocarbon radical which is    unsubstituted or substituted and, including substituents, has from 1    to 20 carbon atoms, preferably from 1 to 10 carbon atoms, for    example (C₁-C₄)alkyl, (C₃-C₄)alkenyl or (C₃-C₄)alkynyl, where each    of the three last-mentioned radicals is unsubstituted or substituted    by one or more radicals selected from the group consisting of    halogen, (C₁-C₄)alkoxy and (C₁-C₄)alkylthio,-   W is an oxygen or sulfur atom,-   X,Y independently of one another are a hydrogen atom, halogen,    (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio, where each of the 3    last-mentioned radicals is unsubstituted or substituted by one or    more radicals selected from the group consisting of halogen,    (C₁-C₄)alkoxy and (C₁-C₄)alkylthio, or are mono- or    di[(C₁-C₄)alkyl]amino, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl,    (C₃-C₆)alkenyloxy or (C₃-C₆)alkynyloxy, and-   V, Z independently of one another are CH or N.

The compounds of the formula (I) can form salts where the hydrogen ofthe —SO₂—NH— group is replaced by an agriculturally suitable cation.These salts are, for example, metal salts, in particular alkali metalsalts or alkaline-earth metal salts, in particular sodium salts andpotassium salts, or else ammonium salts or salts with organic amines.Likewise, salt formation can be carried out by adding an acid to basicgroups, such as, for example, amino and alkylamino. Suitable acids forthis purpose are strong inorganic and organic acids, for example HCl,HBr, H₂SO₄ or HNO₃.

In the formula (I), the two radicals R⁰ and R^(#), R² and R³ and R* andR¹ together can in each case form a nitrogen-containing heterocyclicring.

Carbon-containing radicals are organic radical containing at least onecarbon atom, preferably from 1 to 30 carbon atoms, particularlypreferably from 1 to 20 carbon atoms, and furthermore at least one atomof one or more other elements of the Periodic Table of the Elements,such as H, Si, N, P, S, F, Cl, Br or I. Examples of carbon-containingradicals are unsubstituted or substituted hydrocarbon radicals, whichcan be attached to the skeleton directly or via a heteroatom such as N,S, P or O, unsubstituted or substituted heterocyclyl radicals,carbon-containing acyl radicals or cyano.

In the formula (I) and all the formulae below, the carbon-containingradicals, such as alkyl alkoxy, haloalkyl, haloalkoxy, alkylamino andalkylthio, and the corresponding unsaturated and/or substitutedradicals, can in each case be straight-chain or branched in the carbonskeleton. Unless specifically stated otherwise, the lower carbonskeletons, for example those having 1 to 6 carbon atoms, or in the caseof unsaturated groups those having 2 to 6 carbon atoms, are preferredfor these radicals. Alkyl radicals, also in the composed meanings suchas alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- ori-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl,i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyland 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meaning ofthe unsaturated radicals which are possible and which correspond to thealkyl radicals; alkenyl denotes, for example, allyl,1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl,but-3-en-1-yl, 1-methylbut-3-en-1-yl; and 1-methylbut-2-en-1-yl; alkynylis, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl,1-methylbut-3-yn-1-yl.

Alkenyl in the form (C₃-C₄)alkenyl, (C₃-C₅)alkenyl, (C₃-C₆)alkenyl,(C₃-C₈)alkenyl or (C₃-C₁₂)alkenyl is preferably an alkenyl radicalhaving 3 to 4, 3 to 5, 3 to 6, 3 to 8 and 3 to 6 carbon atoms,respectively, where the double bond is not located at the carbon atomwhich is linked to the remainder of the molecule of the compound (I)(“yl” position). This applies correspondingly to (C₃-C₄)alkynyl etc.,(C₃-C₄)alkenyloxy etc. and (C₃-C₄)alkynyloxy etc.

Cycloalkyl is a carbocyclic saturated ring system having 3-8 carbonatoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Nitrogen-containing radicals which do not contain any carbon areradicals which preferably contain from 1 to 10 nitrogen atoms,particularly preferably 1 or 2 nitrogen atoms, and furthermorepreferably one or more atoms of one or more elements of the PeriodicTable of the Elements which are different from carbon, such as H, O orS. Examples of nitrogen-containing radicals which do not contain anycarbon are NH₂, NO₂, NHOH, NO, NH—NH₂ or N₃.

Halogen is, for example, fluorine, chlorine, bromine or iodine.Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or alkynyl which arepartially or fully substituted by halogen, preferably by fluorine,chlorine and/or bromine, in particular by fluorine or chlorine, forexample CF₃, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl; CCl₃, CHCl₂, CH₂CH₂Cl;haloalkoxy is, for example, OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ andOCH₂CH₂Cl; this applies correspondingly to haloalkenyl and otherhalogen-substituted radicals.

A hydrocarbon radical has a straight-chain, branched or cyclic andsaturated or unsaturated aliphatic or aromatic hydrocarbon radical, forexample alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl; arylin this context is a mono-, bi- or polycyclic aromatic system, forexample phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl,pentalenyl, fluorenyl and the like, preferably phenyl; a hydrocarbonradical is preferably alkyl, alkenyl or alkynyl having up to 12 carbonatoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl.

A heterocyclic radical or ring (heterocyclyl) can be saturated,unsaturated or heteroaromatic and substituted or unsubstituted;preferably, it contains one or more heteroatoms in the ring, preferablyselected from the group consisting of N, O and S; it is preferably analiphatic heterocyclyl radical having 3 to 7 ring atoms or aheteroaromatic radical having 5 or 6 ring atoms and contains 1, 2 or 3heteroatoms. The heterocyclic radical can be, for example, aheteroaromatic radical or ring (heteroaryl), such as, for example, amono-, bi- or polycyclic aromatic system in which at least one ringcontains one or more heteroatoms, for example pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, oxazolyl, furyl,pyrrolyl, pyrazolyl and imidazolyl, or it is a partially or fullyhydrogenated radical, such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl,piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. Substituentswhich are suitable for a substituted heterocyclic radical are thesubstituents mentioned further below, and additionally also oxo. The oxogroup can also be present on the hetero ring atoms which may exist atvarious oxidation levels, for example in the case of N and S.

Substituted radicals, such as substituted hydrocarbon radicals, forexample substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, orsubstituted heterocyclyl or heteroaryl are, for example, a substitutedradical which is derived from the unsubstituted skeleton, thesubstituents being, for example, one or more, preferably 1, 2 or 3,radicals selected from the group-consisting of halogen, alkoxy,haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido,alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- anddialkylaminocarbonyl, substituted amino, such as acylamino, mono- anddialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl,haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl andhaloalkyl, and also unsaturated aliphatic radicals which correspond tothe abovementioned saturated hydrocarbon-containing radicals, such asalkenyl, alkynyl, alkenyloxy, alkynyloxy, etc. Preferred among radicalshaving carbon atoms are those having 1 to 4 carbon atoms, in particular1 or 2 carbon atoms. Preferred are, in general, substituents selectedfrom the group consisting of halogen, for example fluorine and chlorine,(C₁-C₄)alkyl, preferably methyl or ethyl, (C₁-C₄)haloalkyl, preferablytrifluoromethyl, (C₁-C₄)alkoxy, preferably methoxy or ethoxy,(C₁-C₄)haloalkoxy, nitro and cyano. Especially preferred in this contextare the substituents methyl, methoxy and chlorine.

Phenyl which may be substituted is preferably phenyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkyl, (C₁-C₄)haloalkoxy and nitro, for example o-, m- andp-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5- and2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.

Mono- or disubstituted amino is a chemically stable radical selectedfrom the group consisting of the substituted amino radicals, which areN-substituted, for example, by one or two identical or differentradicals selected from the group consisting of alkyl, alkoxy, acyl andaryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino,N-alkyl-N-arylamino and N-heterocycles; preferred in this context arealkyl radicals having 1 to 4 carbon atoms; aryl is in this contextpreferably phenyl or substituted phenyl; acyl is as defined furtherbelow, preferably formyl, (C₁-C₄)alkylcarbonyl or (C₁-C₄)alkylsulfonyl.This applies correspondingly to substituted hydroxylamino or hydrazino.

An acyl radical is the radical of an organic acid which is formedformally by eliminating an OH group from the organic acid, for examplethe radical of a carboxylic acid and radicals of acids derivedtherefrom, such as thiocarboxylic acid, unsubstituted or N-substitutediminocarboxylic acids or the radicals of carbonic monoesters,unsubstituted or N-substituted carbamic acids, sulfonic acids, sulfinicacids, phosphonic acids and phosphinic acids.

A preferred acyl radical is formyl or aliphatic acyl selected from thegroup consisting of CO—R^(x), CS—R^(x), CO—OR^(X), CS—OR^(x), CS—SR^(x),SOR^(Y) or SO₂R^(Y), where R^(x) and R^(Y) are in each case aC₁-C₁₀-hydrocarbon radical which is unsubstituted or substituted, oraminocarbonyl or aminosulfonyl, where the two last-mentioned radicalsare unsubstituted, N-monosubstituted or N,N-disubstituted.

Acyl is, for example, formyl, haloalkylcarbonyl, alkylcarbonyl such as(C₁-C₄)alkylcarbonyl, phenylcarbonyl, where the phenyl ring may besubstituted, for example as shown above for phenyl, or alkyloxycarbonyl,phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl,N-alkyl-1-iminoalkyl and other radicals of organic acids.

The invention also provides all stereoisomers embraced by formula (I)and mixtures of these. Such compounds of the formula (I) contain one ormore asymetric carbon atoms or else double bonds which are not mentionedseparately in the formula (I). Formula (I) embraces all possiblestereoisomers which are defined by their specific spatial form, such asenantiomers, diastereomers and Z and E isomers, they can be obtained bycustomary methods from mixtures of the stereoisomers or be prepared bystereoselective reactions in combination with the use ofstereochemically pure starting materials.

The abovementioned examples of radicals or ranges of radicals which comeunder the general terms such as “alkyl”, “acyl”, “substituted radicals”,etc., are not meant to be complete lists. The general terms also includethe definitions of ranges of radicals in groups of preferred compoundsgiven further below, in particular ranges of radicals which includespecific radicals from the examples in the tables.

Compounds of the formula (I) according to the invention or their saltswhich are of particular interest, mainly for reasons of higherherbicidal activity, better selectivity and/or because they can beprepared more easily are those in which

-   R¹ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, where each of    the three last-mentioned radicals is unsubstituted or substituted by    one or more radicals selected from the group consisting of halogen,    unsubstituted and substituted phenyl, unsubstituted and substituted    heterocyclyl having 3 to 6 ring atoms, unsubstituted and substituted    (C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,    [(C₁-C₄)alkoxy]carbonyl and [(C₁-C₄)haloalkoxy]carbonyl, or is    unsubstituted or substituted (C₃-C₆)cycloalkyl, substituted or    unsubstituted (C₃-C₆)cycloalkenyl, unsubstituted or substituted    phenyl, unsubstituted or substituted heterocyclyl having 3 to 6 ring    atoms,    -   where substituted phenyl, substituted heterocyclyl, substituted        cycloalkyl or substituted cycloalkenyl carry, as substituents,        one or more radicals selected from the group consisting of        halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)alkyl, di[(C₁-C₄)alkoxy](C₁-C₄)alkyl, (C₁-C₄)haloalkoxy,        (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,        (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,        (C₁-C₄)haloalkylsulfonyl, NR⁸R⁹, [(C₁-C₄)alkoxy]carbonyl,        [(C₁-C₄)haloalkoxy]carbonyl, [(C₁-C₄)alkyl]carbonyl, OH, phenyl,        CN and NO₂ and-   R² is a group of the formula R⁰-Q⁰,    -   in which R⁰ is a hydrogen atom, (C₁-C₁₂)alkyl, (C₂-C₁₂)alkenyl        or (C₂-C₁₂)alkynyl, where each the three last-mentioned radicals        is unsubstituted or substituted by one or more radicals selected        from the group consisting of halogen, (C₁-C₆)alkoxy,        (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio,        (C₁-C₆)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl,        (C₁-C₆)alkylsulfonyl, (C₁-C₆)haloalkylsulfonyl,        [(C₁-C₆)alkoxy]carbonyl, [(C₁-C₆)haloalkoxy]carbonyl, CONR⁶R⁷,        SO₂NR⁶R⁷, CN, OH, SH, (C₃-C₆)cycloalkyl, NR⁸R⁹, unsubstituted or        substituted phenyl, unsubstituted or substituted heterocyclyl,        or    -   is (C₃-C₆)cycloalkyl, (C₃-C₆)cycloalkenyl, phenyl or        heterocyclyl, preferably having 3 to 6 ring atoms, where the        four last-mentioned radicals may be unsubstituted or        substituted, and    -   in which Q⁰ is a direct bond or a divalent group of the formula        —O— or —N(R^(#))— where R^(#) is a hydrogen atom, an acyl        radical or (C₁-C₁₂)alkyl, (C₂-C₁₂)alkenyl or (C₂-C₁₂)alkynyl,        where each of the 3 last-mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,        (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, CN, OH,        (C₃-C₆)cycloalkyl, unsubstituted or substituted phenyl,        unsubstituted or substituted heterocyclyl, or is unsubstituted        or substituted (C₃-C₆)cycloalkyl, unsubstituted or substituted        (C₃-C₆)cycloalkenyl or    -   unsubstituted or substituted phenyl, and R⁰ and R^(#) together        with the nitrogen atom of the NR^(#)R⁰ group may form a        heterocyclyl radical, preferably having 3 to 6 ring atoms, which        is unsubstituted or substituted, preferably by one or more        radicals selected from the group consisting of halogen,        (C₁-C₆)alkyl, (C₁-C₆)alkoxy, [(C₁-C₆)alkoxy]carbonyl,        (C₁-C₆)haloalkyl and oxo,    -   R³ is a hydrogen atom, (C₁-C₁₂)alkyl, (C₂-C₁₂)alkenyl or        (C₂-C₂)alkynyl, where each of the 3 last-mentioned radicals is        unsubstituted or substituted by one or more radicals selected        from the group consisting of halogen, (C₁-C₆)alkoxy,        (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio,        (C₁-C₆)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl,        (C₁-C₆)alkylsulfonyl, (C₁-C₆)haloalkylsulfonyl,        [(C₁-C₆)alkoxy]carbonyl, [(C₁-C₆)haloalkoxy]carbonyl, CONR⁶R⁷,        SO₂NR⁶R⁷, CN, OH, (C₃-C₆)cycloalkyl, NR⁸R⁹, unsubstituted or        substituted phenyl, unsubstituted or substituted heterocyclyl,        or is unsubstituted or substituted (C₃-C₆)cycloalkyl;        unsubstituted or substituted (C₃-C₆)cycloalkenyl, unsubstituted        or substituted heterocyclyl, preferably having 3 to 6 ring        atoms, or unsubstituted or substituted phenyl, and-   R² and R³ together with the nitrogen atom of the NR²R³ group (N¹)    may form a heterocyclyl radical, preferably having, 3 to 6 ring    atoms, which is unsubstituted or substituted, preferably by one or    more radicals selected from the group consisting of halogen,    (C₁-C₆)alkyl, (C₁-C₆)alkoxy, [(C₁-C₆)alkoxy]carbonyl,    (C₁-C₆)haloalkyl and oxo, where the oxo radical is preferably not    adjacent to the nitrogen atom (N¹), and-   R⁴ independently of one another are halogen, CN, (C₁-C₄)alkyl,    (C₁-C₄)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl, (C₃-C₆)alkenyloxy,    (C₃-C₆)alkynyloxy, where each of the 6 last-mentioned radicals is    unsubstituted or substituted by one or more radicals selected from    the group consisting of halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,    (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkylsulfinyl,    (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkylsulfonyl,    (C₁-C₆)haloalkylsulfonyl, [(C₁-C₆)alkoxy]carbonyl,    [(C₁-C₆)haloalkoxy]carbonyl; CONR⁶R⁷, SO₂NR⁶R⁷, CN, OH,    (C₃-C₆)cycloalkyl, NR⁸R⁹, unsubstituted or substituted phenyl or    unsubstituted or substituted heterocyclyl, or    -   is unsubstituted or substituted (C₃-C₆)cycloalkyl, unsubstituted        or substituted (C₃-C₆)cycloalkenyl, unsubstituted or substituted        heterocyclyl, preferably having 3 to 6 ring atoms, unsubstituted        or substituted phenyl, [(C₁-C₄)alkyl]carbonyl or        [(C₁-C₄)alkoxy]carbonyl, where each of the two last-mentioned        radicals is unsubstituted or substituted in the alkyl moiety by        one or more halogen atoms, or is a radical of the formula        C(O)—NR′—R″, C(S)—NR′—R″, CR′═N-Q¹-R″, S(O)_(m)-Q¹-R″″,        P(O)_(n)(-Q¹-R″″Q²-R″), NR′-Q¹-R″ or NR′″—N═CR′—R″, where R′, R″        and R′″ independently of one another are a hydrogen atom, an        acyl radical or an unsubstituted or substituted        (C₁-C₁₀)hydrocarbon radical, R″″ is a carbon-containing acyl        radical or an unsubstituted or substituted (C₁-C₁₀)hydrocarbon        radical, and Q¹ and Q² independently of one another are a direct        bond or a divalent group of the formula —O— or —N(R⁺)—, where R⁺        is a hydrogen atom, an acyl radical, or an unsubstituted or        substituted (C₁-C₁₀)hydrocarbon radical, and m=0, 1, 2 or 3, and        n=0, 1 or 2, and R′ together with R″, R⁺ together with R′, R⁺        together with R″ or R⁺ together with R″″ may in each case form a        heterocyclyl radical, preferably having 3 to 6 ring atoms,    -   which is unsubstituted or substituted, preferably by one or more        radicals selected from the group consisting of halogen,        (C₁-C₆)alkyl, (C₁-C₆)alkoxy, [(C₁-C₆)alkoxy]carbonyl,        (C₁-C₆)haloalkyl and oxo,-   I is 0, 1 or 2, preferably 0 or 1,-   R⁵ is H or (C₁-C₄)alkyl which is unsubstituted or substituted,-   R⁶ and R⁷ independently of one another are H, (C₁-C₆)alkyl,    (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, unsubstituted or substituted phenyl    or unsubstituted or substituted heterocyclyl or    -   R⁶ and R⁷ together with the nitrogen atom of the NR⁶R⁷ group may        form a heterocyclyl radical having 5 or 6 ring atoms which may        optionally contain one or more additional heteroatoms selected        from the group consisting of N, O and S and which is        unsubstituted or mono- or polysubstituted by radicals selected        from the group consisting of (C₁-C₄)alkyl and oxo, and-   R⁸ and R⁹ independently of one another are (C₁-C₄)alkylcarbonyl,    (C₁-C₄)haloalkylcarbonyl, (C₁-C₄)alkoxycarbonyl or    (C₁-C₄)alkylsulfonyl or together with the nitrogen atom of the NR⁸R⁹    group may form a heterocyclyl radical having 5 or 6 ring atoms which    may optionally contain one or more additional heteroatoms selected    from the group consisting of N, O and S and which is unsubstituted    or mono- or polysubstituted by radicals selected from the group    consisting of (C₁-C₄)alkyl and oxo, and-   Q is O, S or NR*,-   R* is (C₁-C₄)alkyl, (C₃-C₄)alkenyl or (C₃-C₄)alkynyl, where each of    the three last-mentioned radicals is unsubstituted or substituted by    one or more radicals selected from the group consisting of halogen,    (C₁-C₄)alkoxy and (C₁-C₄)alkylthio, and    -   R* and R¹ together with the nitrogen atom of the NR*R¹ group may        form a heterocyclyl radical which is unsubstituted or        substituted, preferably by one or more radicals selected from        the group consisting of halogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy,        [(C₁-C₆)alkoxy]carbonyl, (C₁-C₆)haloalkyl and oxo,-   X, Y independently of one another are H, halogen, (C₁-C₄)alkyl,    (C₁-C₄)alkoxy, (C₁-C₄)alkylthio, where each of the three    last-mentioned radicals is unsubstituted or substituted by one or    more radicals from the group consisting of halogen, (C₁-C₄)alkoxy    and (C₁-C₄)alkylthio, are mono- or di[(C₁-C₄)alkyl]amino,    (C₃-C₅)alkenyl, (C₃-C₅)alkenyloxy, (C₃-C₅)alkynyl or    (C₃-C₅)alkynyloxy, and    where the radicals R¹, R², R³ and R⁴, including substituents, have    up to 20 carbon atoms.

Of particular interest are compounds of the formula (I) according to theinvention in which

-   R¹ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl or (C₃-C₆)alkynyl, where each    of the three last-mentioned radicals is unsubstituted or substituted    by one or more radicals selected from the group consisting of    halogen, phenyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₃-C₆)cycloalkyl,    heterocyclyl having 3 to 6 ring atoms and [(C₁-C₄)alkoxy]carbonyl,    or is (C₃-C₆)cycloalkyl or heterocyclyl having 3 to 6 ring atoms,    where each of the two last-mentioned radicals is unsubstituted; or    substituted by one or more radicals selected from the group    consisting of halogen, (C₁-C₄)alkyl and (C₁-C₄)alkoxy,-   R² is a group of the formula R⁰-Q⁰- in which    -   R⁰ is a hydrogen atom, (C₁-C₈)alkyl, (C₃-C₈)alkenyl or        (C₃-C₈)alkynyl, where each of the 3 last-mentioned radicals is        unsubstituted or substituted by one or more radicals selected        from the group consisting of halogen, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,        (C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl,        (C₁-C₄)alkylsulfonyl, (C₁-C₄)haloalkylsulfonyl,        [(C₁-C₆)alkoxy]carbonyl, CONR⁶R⁷, SO₂NR⁶R⁷, CN, OH,        (C₃-C₆)cycloalkyl, NR⁸R⁹ and phenyl which is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,        (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, NR⁸R⁹,        [(C₁-C₄)alkoxy]carbonyl, [(C₁-C₄)alkyl]carbonyl, phenyl,        [(C₁-C₄)alkyl]carbonyl, CN and NO₂, or    -   is heterocyclyl having 3 to 6 ring atoms which is unsubstituted        or substituted by one or more radicals selected from the group        consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,        (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, NR⁸R⁹,        [(C₁-C₄)alkoxy]carbonyl, [(C₁-C₄)alkyl]carbonyl, phenyl, CN and        NO₂, or is (C₃-C₆)cycloalkyl which ist unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,        (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, [(C₁-C₄)alkoxy]carbonyl, CN,        OH and phenyl, or    -   is (C₃-C₆)cycloalkenyl which is unsubstituted or substituted by        one or more radicals selected from the group consisting of        halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and        [(C₁-C₄)alkoxy]carbonyl, or    -   is phenyl which is unsubstituted or substituted by one or more        radicals selected from the group consisting of halogen,        (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,        (C₁-C₄)alkylsulfonyl, NR⁸R⁹, [(C₁-C₄)alkoxy]carbonyl,        [(C₁-C₄)alkyl]carbonyl, phenyl, CN and NO₂, and    -   Q⁰ is a direct bond or a divalent group of the formula —O— or        —NR^(#), in which R^(#) is a hydrogen atom or unsubstituted or        substituted (C₁-C₄)alkyl,-   R³ is a hydrogen atom, (C₁-C₈)alkyl, (C₃-C₈)alkenyl or    (C₃-C₈)alkynyl, where each of the 3 last-mentioned radicals is    unsubstituted or substituted by one or more radicals selected from    the group consisting of halogen, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,    (C₁-C₄)haloalkylsulfonyl, [(C₁-C₆)alkoxy]carbonyl, CONR⁶R⁷,    SO₂NR⁶R⁷, CN, OH, (C₃-C₆)cycloalkyl; NR⁸R⁹ and phenyl which is    unsubstituted or substituted by one or more radicals selected from    the group consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,    (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsufonyl, NR⁸R⁹,    [(C₁-C₄)alkoxy]carbonyl, [(C₁-C₄)alkyl]carbonyl, phenyl,    [(C₁-C₄)alkyl]carbonyl, CN and NO₂, or is heterocyclyl preferably    having 3 to 6 ring atoms which is unsubstituted or substituted by    one or more radicals selected from the group consisting of halogen,    (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, NR⁸R⁹,    [(C₁-C₄)alkoxy]carbonyl, [(C₁-C₄)alkyl]carbonyl, phenyl, CN and NO₂,    or is (C₃-C₆)cycloalkyl which is unsubstituted or substituted by one    or more radicals selected from the group consisting of halogen,    (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,    [(C₁-C₄)alkoxy]carbonyl, CN, OH and phenyl, or    -   is (C₃-C₆)cycloalkenyl which is unsubstituted or substituted by        one or more radicals selected from the group consisting of        halogen; (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy and        [(C₁-C₄)alkoxy]carbonyl, or    -   is phenyl which is unsubstituted or substituted by one or more        radicals selected from the group consisting of halogen,        (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,        (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,        (C₁-C₄)alkylsulfonyl, NR⁸R⁹, [(C₁-C₄)alkoxy]carbonyl,        [(C₁-C₄)alkyl]carbonyl, phenyl, CN and NO₂, and-   R² and R³ together with the nitrogen atom (N¹) may form a    heterocyclyl radical of 3-6 ring atoms which may be saturated,    unsaturated or heteroaromatic and may, in addition to the nitrogen    atom (N¹), contain one or two heteroatoms selected from the group    consisting of N, O and S and which is unsubstituted or substituted    by one or more radicals selected from the group consisting of    (C₁-C₆)alkyl, preferably (C₁-C₃)alkyl, (C₁-C₃)alkoxy, halogen,    [(C₁-C₃)alkoxy] carbonyl, (C₁-C₃)haloalkyl and oxo, where the oxo    radical is preferably not adjacent to the nitrogen atom (N¹),-   R⁴ are halogen, CN, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₆)alkenyl,    (C₂-C₆)alkynyl, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy,    -   where each of the 6 last-mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, (C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy,        (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, (C₁-C₆)alkylsulfinyl,        (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkylsulfonyl,        (C₁-C₆)-haloalkylsulfinyl, [(C₁-C₆)alkoxy]carbonyl,        [(C₁-C₆)haloalkoxy]carbonyl, CONR⁶R⁷, SO₂NR⁶R⁷, CN, OH,        (C₁-C₆)cycloalkyl, NR⁸R⁹, unsubstituted or substituted phenyl,        unsubstituted or substituted heterocyclyl, or    -   are unsubstituted or substituted, (C₃-C₆)cycloalkyl,        unsubstituted or substituted (C₃-C₆)cycloalkenyl, unsubstituted        or substituted heterocyclyl having 3 to 6 ring atoms,        unsubstituted or substituted phenyl or [(C₁-C₄)alkyl]carbonyl or        [(C₁-C₄)alkoxy]carbonyl, where each of the two last-mentioned        radicals is unsubstituted or substituted in the alkyl moiety by        one or more halogen atoms, or are radicals of the formula        C(O)—NR′—R″, C(S)—NR′—R″, CR′═N-Q¹-R″, NR′-Q¹-R″ or NR″—N═CR′—R″        where R′, R″ and R′″ independently of one another are a hydrogen        atom, an acyl radical or an unsubstituted or substituted        (C₁-C₁₀)hydrocarbon radical, and Q¹ and Q² independently of one        another are a direct bond or a divalent group of the formula —O—        or —N(R⁺)—, where R⁺ is a hydrogen atom, an acyl radical or an        unsubstituted or substituted (C₁-C₄)alkyl radical and R′        together with R″ or R⁺ together with R′ or R⁺ together with R″        may in each case form a heterocyclyl radical having 3 to 6 ring        atoms which is, unsubstituted or substituted, preferably by one        or more radicals selected from the group consisting of halogen,        (C₁-C₆)alkyl, (C₁-C₆)alkoxy, [(C₁-C₆)alkoxy]carbonyl,        (C₁-C₆)haloalkyl and oxo,-   I is 0 or 1,-   R⁶ and R⁷ independently of one another are H, (C₁-C₄)alkyl,    (C₃-C₄)alkenyl, (C₃-C₄)alkynyl or phenyl which is unsubstituted or    substituted by one or more radicals selected from the group    consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,    (C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfonyl,    [(C₁-C₄)alkoxy]carbonyl, CN and NO₂, or-   R⁶ and R⁷ together with the nitrogen atom of the NR⁶R⁷ group may    form a heterocyclyl radical having 5 or 6 ring members which may    contain one or more heteroatoms selected from the group consisting    of N, O and S and which is unsubstituted or mono- or polysubstituted    by radicals selected from the group consisting of (C₁-C₄)alkyl and    oxo,-   R⁸ and R⁹ are (C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl,    (C₁-C₄)alkoxycarbonyl or (C₁-C₄)alkylsulfonyl, or together with the    nitrogen atom of the NR⁸R⁹ group may form a heterocyclyl radical    having 5 or 6 ring members which may contain one or more heteroatoms    selected from the group consisting of N, O and S and which is    unsubstituted or mono- or polysubstituted by radicals selected from    the group consisting of (C₁-C₄)alkyl and oxo.

Also of particular interest are compounds of the formula (I) accordingto the invention and salts thereof in which

-   R¹ is (C₁-C₆)alkyl which is unsubstituted or substituted by one or    more radicals selected from the group consisting of halogen and    (C₁-C₄)alkoxy, or is 3-oxetanyl, (C₃-C₄)alkenyl or (C₃-C₄)alkynyl,-   R² is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, where each of    the three last-mentioned radicals is unsubstituted or substituted by    one or more radicals selected from the group consisting of halogen,    (C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfonyl,    [(C₁-C₄)alkoxy]carbonyl, (C₃-C₆)cycloalkyl, CN and OH, or    -   is (C₃-C₆)cycloalkyl which is unsubstituted or substituted by        one or more radicals selected from the group consisting of        halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, [(C₁-C₄)alkoxy]carbonyl,        CN and OH, or is (C₃-C₆)cycloalkenyl, (C₁-C₄)alkoxy,        (C₁-C₄)alkenyloxy, (C₁-C₄)alkylamino or di[(C₁-C₄)alkyl]amino        and-   R³ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, where each of    the three last-mentioned radicals is unsubstituted or substituted by    one or more radicals selected from the group consisting of halogen,    (C₁-C₄)alkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfonyl,    [(C₁-C₄)alkoxy]carbonyl, (C₃-C₆)cycloalkyl, CN and OH, or    -   is (C₃-C₆)cycloalkyl which is unsubstituted or substituted by        one or more radicals selected from the group consisting of        halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, [(C₁-C₄)alkoxy]carbonyl,        CN and OH, or is (C₃-C₆)cycloalkenyl or.-   R² and R³ together with the nitrogen atom (N¹) may form a    heterocyclyl radical of 3-6, preferably 5 or 6 ring atoms which is    saturated, unsaturated or heteroaromatic, which may, in addition to    the nitrogen atom (N¹), contain one or two heteroatoms selected from    the group consisting of N, O and S and which is unsubstituted or    substituted by one or more radicals selected from the group    consisting of halogen, (C₁-C₆)alkyl, preferably (C₁-C₃)alkyl,    (C₁-C₃)alkoxy, [(C₁-C₃)alkoxy]carbonyl and oxo, where the oxo    radical is preferably not adjacent to the nitrogen atom (N¹), and-   R⁴ are (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy or halogen,-   I is 0 or 1, preferably 0,-   R⁵ is H or methyl,-   Q is O or NR*,-   R* is H or (C₁-C₄)alkyl,-   X and Y independently of one another are (C₁-C₄)alkyl,    (C₁-C₄)alkoxy, where each of the two last-mentioned radicals is    unsubstituted or substituted by one or more halogen atoms, or are    (C₁-C₄)alkylthio, halogen or mono-oder di[(C₁-C₂)alkyl]amino, and-   W is an oxygen atom.

Preferred compounds of the formula (I) according to the invention orsalts thereof are those in which

-   R¹ is (C₁-C₃)alkyl, allyl or propargyl,-   R² is H, (C₁-C₄)alkyl, (C₃-C₅)alkenyl, (C₃-C₅)alkynyl,    (C₃-C₆)cycloalkyl or (C₃-C₆)cycloalkenyl,-   R³ is H, (C₁-C₄)alkyl, (C₃-C₅)alkenyl, (C₃-C₅)alkynyl,    (C₃-C₆)cycloalkyl or (C₃-C₆)cycloalkenyl, or-   R² and R³ together with the nitrogen atom (N¹) may form a    heterocyclyl radical of 3-6, preferably 5 or 6 ring atoms which is    saturated, unsaturated or heteroaromatic, which may, in addition to    the nitrogen atom (N¹), contain one or two heteroatoms selected from    the group consisting of N, O and S and which is unsubstituted or    substituted by one or more (C₁-C₆) alkyl radicals,-   R⁴ are (C₁-C₃)alkyl or halogen,-   I is 0 or 1, preferably 0,-   Q is O or NR*,-   R* is (C₁-C₃)alkyl,-   X is (C₁-C₂)alkyl, (C₁-C₂)alkoxy, (C₁-C₂)alkylthio, (C₁-C₂)haloalkyl    or (C₁-C₂)haloalkoxy,-   Y is (C₁-C₂)alkyl, (C₁-C₂)alkoxy, halogen, NHCH₃ or N(CH₃)₂,-   V is CH or N, preferably N and-   Z is CH or N.

Particularly preferred compounds of the formula (I) according to theinvention are salts thereof are those in which

-   R¹ is (C₁-C₃)alkyl, allyl or propargyl and/or-   Q is an oxygen atom.

Particular preference is also given to compounds of the formula (I)according to the invention and salts thereof which contain a combinationof radicals from the abovementioned compounds of particular interest orthe preferred compounds, and also to those which contain one or moreradicals from the compounds listed in Tables 1 and 2 (see below).Preference is likewise given to compounds of the formula (I) in whichV=N.

The present invention also provides processes for preparing thecompounds of the formula (I) according to the invention or saltsthereof, which comprise

-   a) reacting a compound of the formula (II)    -   with a heterocyclic carbamate of the formula (III),    -   in which R** is a substituted or unsubstituted        C₁-C₂₀-hydrocarbon radical, such as aryl or alkyl, preferably        unsubstituted or substituted phenyl or unsubstituted or        substituted (C₁-C₄)alkyl, or-   b) reacting a sulfonylcarbamate of the formula (IV),    -   in which R*** is a substituted or unsubstituted        C₁-C₂₀-hydrocarbon radical, such as unsubstituted or substituted        phenyl or unsubstituted or substituted (C₁-C₄)alkyl, with an        amino heterocycle of the formula (V)    -   or-   c) reacting a sulfonyl isocyanate of the formula (VI)    -   with an amino heterocycle of the formula (V) or-   d) reacting a sulfonamide of the formula (II) with a    (thio)isocyanate of the formula (VII)    -   in the presence of a base or-   e) reacting an amino heterocycle of the formula (V) initially under    base catalysis with a carbonic ester, for example diphenyl    carbonate, and reacting the resulting intermediate in a one-pot    reaction with a sulfonamide of the formula (II) (see variant a), or-   f) reacting a phenylsulfonyl urea of the formula (VIII)    -   by reduction of the nitro group and, if appropriate, further        conversion of the hydroxylamine or amine function that is        released to give a sulfonyl urea of the formula (I),        where in the formulae (II)-(VIII) the radicals, groups and        indices R¹-R⁵, Q, V, W, X, Y, Z and I are as defined in formula        (I). Process variants a) to c), e) and f) initially afford        compounds of the formula (I) where W═O.

The reaction of the compounds of the formulae (II) and (III) ispreferably carded out under base catalysis in an inert organic solvent,such as, for example, dichloromethane, acetonitrile, dioxane or THF, attemperatures between 0° C., preferably 20° C., and the boiling point ofthe solvent. The base used is, for example, an organic amine base, suchas 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), an alkali metaltert-butoxide, such as, for example, NaO-t-C₄H₉, or an alkali metalhydroxide, such as, for example, NAOH, in particular if R**=(subst.)phenyl (cf. EP-A-44 807), or trimethylaluminum or triethylaluminum, thelatter in particular if R**=alkyl (cf. EP-A-166 516). The base inquestion is employed here, for example, in the range of from 1 to 3molar equivalents, based on the compound of the formula (II).

The sulfonamides (II) and structurally related compounds of the formulae(IV) and (VI) and the phenylsulfonylureas (VIII) are novel compounds.They, and their preparation, likewise form part of the subject-matter ofthe present invention.

The compounds of the formula (II) are obtained as shown in Scheme 1, forexample starting with compounds of the formula (IX)

Treatment of sulfonyl chlorides of the formula (IX) with “tertbutylamine gives sulfonamides of the formula (X). By reducing the nitrogroups in the compounds of the formula (X), the correspondinghydroxylamines or amines (XI′) are obtained, and the functionality thatis released can, if appropriate, be derivatized, for example alkylated.The resulting intermediates of the formula (XI) are finally convertedinto the compounds (II), by treatment with acid. The radicals R¹ to R⁴,Q and I in Scheme 1 are as defined in formula (I).

Sulfonamide formation is carried out, for example, in inert solvents,such as, for example, dichloromethane, tetrahydrofuran (THF), dioxane,toluene or dimethylformamide (DMF), at temperatures from −70° C. to theboiling point of the solvent, preferably of up to 25° C. Here,preference is given to using an amount of amine of 1.5-2.5 equivalents,based on the sulfonyl chloride.

The reduction of the nitro function in (X) to amines or hydroxylaminesof the formula (XI′) is carried out similarly to known methods (cf.Houben-Weyl, “Methoden der Organischen Chemie” [Methods of OrganicChemistry], 4th Ed. Vol. XI/1 pp. 360 ff, Thieme Verlag Stuttgart, 1957and Vol. X/1 pp. 1138 ff, Thieme Verlag Stuttgart, 1971).

Compounds of the formula (XI′) (where n=0), can be subjected toreductive alkylation with carbonyl compounds (cf. Houben-Weyl, “Methodender Organischen Chemie”, 4th Ed. Vol. XI/1 pp. 618-643, Thieme VerlagStuttgart, 1957; J. Am. Chem. Soc. 96 (1974) 7812-7814; J. Med. Chem. 38(1995) 3132-3137). By subsequent cleavage of the tert-butyl group, it ispossible to prepare, for example, secondary and tertiary anilines of theformula (II).

In the compounds (XI), the tert-butyl protective group is removed bytreatment with a strong acid (see WO 89/10921). Suitable strong acidsare, for example, mineral acids, such as H₂SO₄ or HCl, or strong organicacids, such as trifluoroacetic acid. The reaction is carried out, forexample, at temperatures of from −20° C. to the respective refluxtemperature of the reaction mixture, preferably at from 0° C. to 40° C.The reaction can be carried out in the absence of a solvent or else inan inert solvent, such as, for example, dichloromethane ortrichloromethane.

For I=0, Q=O and R¹=H, Me, Et and allyl, the compounds (IX) are known(see U.S. Pat. No. 4,647,588, U.S. Pat. No. 4,694,020, EP-A-197 386 andU.S. Pat. No. 4,603,133). The novel compounds of the formula (IX)according to the invention can be prepared starting withring-substituted phthalic acids (for I=0 for example from commercial3-nitrophthalic acid), similarly to known methods (see J. HeterocyclicChem. 23 (1986) 1253-1255).

The carbamates of the formula (III) can be prepared by methods asdescribed in the South African Patent Applications 82/5671 and 82/5045,or EP-A-70 804 (U.S. Pat. No. 4,480,101) or RD 275 056.

The reaction of the compounds (IV) with the amino heterocycles (V) ispreferably carried out in inert aprotic solvents, such as, for example,dioxane, acetonitrile or tetrahydrofuran, at temperatures between 0° C.and the boiling point of the solvent. The phenylsulfonylcarbamates ofthe formulae (IV) and (XII) are obtained from compounds of the formulae(II) and (XII), respectively, by the methods of U.S. Pat. No. 4,684,393or U.S. Pat. No. 4,743,290. The required starting materials (V) areknown from the literature or can be prepared by processes known from theliterature (see DE-A-38 42 621; Dudley J. R. et al. J. Am. Chem. Soc. 73(1951) 1968-2990; Braker et al. J. Am. Chem. Soc. 69 (1947) 3072, 3075;Rose et al. J. Chem. Soc. (1946) 81, 84; Huffman, K. R.; Schaefer, F. C.J. Org. Chem. 28 (1963) 1816-1821; Gabriel et al. Chem. Ber. 32 (1899)2924).

The phenylsulfonyl isocyanates of the formula (VI) can be preparedsimilarly to U.S. Pat. No. 4,481,029 and reacted with the aminoheterocycles (V).

The (thio)isocyanates of the formula (VII) can be obtained by processesknown from the literature (EP-A-232 067, EP-A-166 516). The(thio)isocyanates (VII) are reacted with the compounds (II), forexample, at from −10° C. to 100° C., preferably at from 20° C. to 100°C., in an inert aprotic solvent, such as, for example, acetone oracetonitrile, in the presence of a suitable base, for exampletriethylamine or potassium carbonate.

The intermediates of the formula (VIII) can be prepared, for example, byavoiding the isolation of the intermediate sulfonyl isocyanates,directly from the sulfonyl chlorides (IX) and the amino heterocycles (V)in the presence of an alkali metal or ammonium cyanate or thiocyanateand pyridine (cf. U.S. Pat. No. 5,157,119). Alternatively, the compounds(VIII) can also be obtained by reacting a sulfonamide (XII) withcarbamates of the formula (III), corresponding to the process describedunder a). Starting with the sulfonamides (XII), the intermediates of theformula (VIII) can also be prepared by the methods of the processesdescribed under d) and e). Moreover, the intermediates of the formula(VIII) can also be prepared from compounds of the formula (X*) whereZ**=NHCOOR***, similarly to the process described under b).

The sulfonamides (XII) can be obtained by reacting the compounds (IX)with ammonia (Scheme 2).

The sulfonamide is formed, for example, in aqueous medium or inertsolvents, such as, for example ethyl acetate, dichloromethane,tetrahydrofuran (THF), dioxane, toluene or dimethylformamide (DMF), attemperatures from −70° C. to the boiling point of the solvent,preferably up to 25° C. Preference is given, to using an amount ofammonium of 1.5-2.5 equivalents, based on the sulfonyl chloride.

The reaction of an amino heterocycle of the formula (V) with diphenylcarbonate and a sulfonamide of the formula (II) can be, carried out in aone-pot reaction in accordance with EP-A-562 575.

The compounds of the formulae (II), (IV), (VI), (XI) and (XI′) mentionedare structurally related novel intermediates of the formula (II*)

in which Z*=NH₂, NHCOOR***, NCO or NH-tert-butyl and R¹-R⁴, I and Q areas defined in formula (I) and R*** is as defined in formula (IV).

The abovementioned compounds of the formulae (IX), (X), (XII) and (XII′)are structurally related novel intermediates of the formula (X*)

in which Z**=NH₂, NHCOOR***, NH-tert-butyl or Cl and R¹, R⁴, I and Q areas defined in formula (I) and R*** is as defined in formula (IV), exceptfor compounds in which Z**=Cl, I=0, Q=O and R¹=H, methyl, ethyl orallyl.

Also novel are the intermediates of the formula (VIII)

in which R¹, R⁴, R⁵, Q, V, W, X, Y, Z and I are as defined in formula(I).

The salts of the compounds of the formula (I) are preferably prepared ininert polar solvents, such as, for example, water, methanol or acetone,at temperatures of from 0° C. to 100° C. Suitable bases for preparingthe salts according to the invention are, for example, alkali metalcarbonates, such as potassium carbonate, alkali metal and alkaline earthmetal hydroxides, for example NaOH or KOH, or alkali metal alkoxides,such as sodium methoxide or sodium tert-butoxide, or ammonia orethanolamine.

The “inert solvents” mentioned in the process variants above are to beunderstood as meaning in each case solvents which are inert under thereaction conditions in question, but which need not be inert under anyreaction conditions.

Collections of compounds of the formula (I) and salts thereof which canbe synthesized by the abovementioned scheme may also be prepared in aparallel manner and this may be effected manually or in a semiautomatedor fully automated manner. In this case, it is possible, for example, toautomate the procedure of the reaction, the work-up or the purificationof the products or of the intermediates. In total, this is to beunderstood as meaning a procedure as is described, for example, by S. H.DeWitt in “Annual Reports in Combinatorial Chemistry and MolecularDiversity: Automated Synthesis”, Volume 1, Verlag Escom 1997, pages 69to 77.

A number of commercially available apparatuses as they are offered by,for example, Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM98SE, England, H+P Labortechnik GmbH, Bruckmannring 28, 85764Oberschleiβheim, Germany or Radleys, Shirehill, Saffron Walden, Essex,CB11 3AZ, England may be used for the parallel procedure of the reactionand work-up. For the parallel purification of compounds of the formula(I) and their salts, or of intermediates obtained during thepreparation, use may be made, inter alia, of chromatography apparatuses,for example those from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr.68504, USA.

The apparatuses mentioned lead to a modular procedure in which theindividual process steps are automated, but manual operations have to beperformed between the process steps. This can be avoided by employingsemi-integrated or fully integrated automation systems where theautomation modules in question are operated by, for example, robots.Such automation systems can be obtained, for example, from ZymarkCorporation, Zymark Center, Hopkinton, Mass. 01748, USA.

In addition to what has been described here, compounds of the formula(I) and salts thereof may be prepared in part or fully bysolid-phase-supported methods. For this purpose, individual intermediatesteps or all intermediate steps of the synthesis or of a synthesisadapted to suit the procedure in question are bound to a syntheticresin. Solid-phase-supported synthesis methods are described extensivelyin the specialist literature, for example Barry A. Bunin in “TheCombinatorial Index”, Verlag Academic Press, 1998.

The use of solid-phase-supported synthesis methods permits a series ofprotocols which are known from the literature and which, in turn, can beperformed manually or in an automated manner. For example, the “tea-bagmethod” (Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl.Acad. Sci, 1985, 82, 5131-5135), in which products from IRORI, 11149North Torrey Pines Road, La Jola, Calif. 92037, USA, are employed, maybe semiautomated. The automation of solid-phase-supported parallelsyntheses is performed successfully, for example, by apparatuses fromArgonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif.94070, USA or MultiSyn Tech GmbH, Wullener Feld 4, 58454 Witten,Germany.

The preparation methods described here give compounds of the formula (I)and their salts in the form of collections of substances known aslibraries. The present invention also relates to libraries which containat least two compounds of the formula (I) and their salts.

The compounds of the formula (I) according to the invention and theirsalts, hereinbelow together referred to as compounds of the formula (I)(according to the invention), have excellent herbicidal activity againsta broad spectrum of economically important monocotyledonous anddicotyledonous harmful plants. The active compounds also act efficientlyon perennial weeds which produce shoots from rhizomes, root stocks orother perennial organs and which are difficult to control. In thiscontext, it is generally immaterial whether the substances are appliedpre-sowing, pre-emergence or post-emergence. Specifically, examples maybe mentioned of some representatives of the monocotyledonous anddicotyledonous weed flora which can be controlled by the compoundsaccording to the invention, without these being a restriction to certainspecies.

Examples of weed species on which the active compounds act efficientlyare, from amongst the monocotyledons, Avena, Lolium, Alopecurus,Phalaris, Echinochloa, Digitaria, Setaria and also Cyperus species fromthe annual sector and from amongst the perennial species Agropyron,Cynodon, Imperata anrd Sorghum, and also perennial Cyperus species.

In the case of the dicotyledonous weed species, the spectrum of actionextends to species such as, for example, Galium, Viola, Veronica,Larnium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilonand Sida from amongst the annuals, and Convolvulus, Cirsium, Rumex andArtemisia in the case of the perennial weeds.

The active ingredients according to the invention also effectoutstanding control of harmful plants which occur under the specificconditions of rice growing such as, for example, Echinochloa,Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus.

If the compounds according to the invention are applied to the soilsurface prior to germination, then the weed seedlings are eitherprevented completely from emerging, or the weeds grow until they havereached the cotyledon stage but then their growth stops, and,eventually, after three to four weeks have elapsed, they die completely.

If the active compounds are applied post-emergence to the green parts ofthe plants, growth also stops drastically a very short time after thetreatment and the weed plants remain at the developmental stage of thepoint in time of application, or they die completely after a certaintime, so that in this manner competition by the weeds, which is harmfulto the crop plants, is eliminated at a very early point in time and in asustained manner.

Although the compounds according to the invention have an excellentherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example, dicotyledonouscrops such as soya, cotton, oilseed rape, or sugar beet, or gramineouscrops such as wheat, barley, rye, rice or corn, in particular soya, arenot damaged at all, or only to a negligible extent. For these reasons,the present compounds are highly suitable for selectively controllingundesired plant growth in plantings for agricultural use or in plantingsof ornamentals.

In addition, the substances according to the invention have outstandinggrowth-regulating properties in crop plants. They engage in the plantmetabolism in a regulating manner and can thus be employed for thetargeted control of plant constituents and for facilitating harvesting,for example, by provoking desiccation and stunted growth. Furthermore,they are also suitable for generally regulating and inhibitingundesirable vegetative growth, without destroying the plants in theprocess. Inhibition of vegetative growth plays an important role in manymonocotyledonous and dicotyledonous crops because lodging can be reducedhere by, or prevented completely.

Owing to their herbicidal and plant growth-regulatory properties, theactive compounds can also be employed for controlling harmful plants incrops of known or still to be developed genetically engineered, plants.The transgenic plants generally have particularly advantageousproperties, for example resistance to certain pesticides, in particularcertain herbicides, resistance to plant diseases or causative organismsof plant diseases, such as certain insects or microorganisms such asfungi, bacteria or viruses. Other particular properties relate, forexample, to the quantity, quality, storage-stability, composition and tospecific ingredients of the harvested product. Thus, transgenic plantshaving an increased starch content or a modified quality of the starchor those having a different fatty acid composition of the harvestedproduct are known.

The use of the compounds of the formula (I) according to the inventionor their salts in economically important transgenic crops of useful andornamental plants, for example of cereal, such as wheat, barley, rye,oats, millet, rice, maniok and corn, or else in crops of sugar beet,cotton, soya, oilseed rape, potato, tomato, pea and other vegetablespecies is preferred.

The compounds of the formula (I) can preferably be used as herbicides incrops of useful plants which are resistant or which have been maderesistant by genetic engineering toward the phytotoxic effects of theherbicides.

Conventional, ways of preparing novel plants which have modifiedproperties compared to known plants comprise, for example, traditionalbreeding methods and the generation of mutants. Alternatively, novelplants having modified properties can be generated with the aid ofgenetic engineering methods (see, for example, EP-A 0 221 044, EP-A 0131 624). For example, there have been described several cases of

-   -   genetically engineered changes in crop plants in order to modify        the starch synthesized in the plants (for example WO 92/11376,        WO 92/14827 and WO. 91/19806),    -   transgenic crop plants which are resistant to certain herbicides        of the glufosinate- (cf., for example, EP-A 0 242 236, EP-A 0        242 246) or glyphosate-type (WO 92/00377), or of the        sulfonylurea-type (EP-A 0 257 993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, having, the ability        to produce Bacillus thuringiensis toxins (Bt toxins) which        impart resistance to certain pests to the plants (EP-A 0 142        924, EP-A 0 193 259),    -   transgenic crop plants, having a modified fatty acid composition        (WO 91/13972).

Numerous molecular biological techniques which allow the preparation ofnovel transgenic plants having modified properties are known inprinciple; see, for example, Sambrook et al., 1989, Molecular Cloning, ALaboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold.Spring. Harbor, N.Y.; or Winnacker “Gene und Klone” [Genes and Clones],VCH Weinheim, 2nd edition 1996, or Christou, “Trends in Plant Science” 1(1996) 423-431).

In order to carry out such genetic engineering manipulations, it ispossible to introduce nucleic acid molecules into plasmids which allow amutagenesis or a change in the sequence to occur by recombination of DNAsequences. Using the abovementioned standard processes it is possible,for example, to exchange bases, to remove partial sequences or to addnatural or synthetic sequences. To link the DNA fragments with eachother, it is possible to attach adaptors or linkers to the fragments.

Plant cells having a reduced activity of a gene product can be prepared,for example, by expressing at least one appropriate antisense-RNA, asense-RNA to achieve a cosuppression effect, or by expressing at leastone appropriately constructed ribozyme which specifically cleavestranscripts of the abovementioned gene product.

To this end, it is possible to employ both DNA molecules which comprisethe entire coding sequence of a gene product including any flankingsequences that may be present, and DNA molecules which comprise onlyparts of the coding sequence, it being necessary for these parts to belong enough to cause an antisense effect in the cells. It is alsopossible to use DNA sequences which have a high degree of homology tothe coding sequences of a gene product but which are not entirelyidentical.

When expressing nucleic acid molecules in plants, the synthesizedprotein can be localized in any desired compartment of the plant cells.However, to achieve localization in a certain compartment, it is, forexample, possible to link the coding region with DNA sequences whichensure localization in a certain compartment. Such sequences are knownto the person skilled in the art (see, for example, Braun et al., EMBOJ. 11 (19902), 32193227; Wolter et al., Proc. Natl. Acad. Sci. USA 85(1988), 846-850; Sonnewald et al., Plant j. 1 (1991), 95-106).

The transgenic plant cells can be regenerated to whole plants usingknown techniques. The transgenic plants can in principle be plants ofany desired plant species, i.e. both monocotyledonous and dicotyledonousplants.

In this manner, it is possible to obtain transgenic plants which havemodified properties by overexpression, suppression or inhibition ofhomologous (=natural) genes or gene sequences or by expression ofheterologous (=foreign) genes or gene sequences.

The compounds according to the invention can preferably be used intransgenic crops which are resistant to herbicides selected from thegroup consisting of the sulfonylureas, glufosinate-ammonium orglyphosate-isopropylammonium and analogous active compounds.

When using the active compounds according to the invention in transgeniccrops, in addition to the effects against harmful plants which can beobserved in other crops, there are frequently effects which are specificfor the application in the respective transgenic crop, for example amodified or specifically broadened spectrum of weeds which can becontrolled, modified application rates which can be used for theapplication, preferably good combinability with the herbicides to whichthe transgenic crops are resistant, and an effect on the growth and theyield of the transgenic crop plants.

The invention therefore also provides for the use of the compounds (I)according to the invention as herbicides for controlling harmful plantsin transgenic crop plants.

The compounds according to the invention can be applied in the customaryformulations in the form of wettable powders, emulsifiable concentrates,sprayable solutions, dusts or granules. The invention therefore alsoprovides herbicidal and plant growth-regulating compositions comprisingcompounds of the formula (I).

The compounds of the formula (I) can be formulated in various waysdepending on the prevailing biological and/or chemico-physicalparameters. Examples of suitable formulation options are: wettablepowders (WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), oil- or water-based dispersions, oil-miscible solutions, capsulesuspensions (CS), dusts (DP), seed-dressing compositions, granules forbroadcasting and soil application, granules (GR) in the form ofmicrogranules, spray granules, coating granules and adsorption granules,water-dispersible granules (WG), water-soluble granules (SG), ULVformulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in Winnacker-Kuchler, “Chemische Technologie”[Chemical Technology], Volume 7, C. Hauser Veriag Munich, 4th edition1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker,N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G.Goodwin Ltd. London.

The necessary formulation auxiliaries, such as inert materials,surfactants, solvents and other additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd ed., Darland Books, Caldwell. N.J., H.v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Greenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxideadducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie” [Chemical Technology], Volume 7, C. HauserVerlag Munich, 4th edition 1986.

Based on these formulations it is also possible to produce combinationswith other pesticidally active substances, for example insecticides,acaricides, herbicides and fungicides, and also with safeners,fertilizers and/or growth regulators, for example in the form of aready-mix or tank mix.

Wettable powders are preparations which are uniformly dispersible inwater and which contain, in addition to the active compound and as wellas a diluent or inert substance, surfactants of ionic and/or nonionictype (wetting agents, dispersants), for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines;fatty alcohol polyglycol ethersulfates, alkanesulfonates,alkylbenzenesulfonates, sodium ligninsulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate. Toprepare the wettable powders, the herbicidally active compounds arefinely ground, for example in customary apparatus such as hammer mills,fan mills and air-jet mills, and are mixed simultaneously orsubsequently with the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents, with the addition ofone or more surfactants of ionic and/or nonionic type (emulsifiers).Examples of emulsifiers which can be used are calciumalkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionicemulsifiers, such as fatty acid polyglycol esters, alkylaryl polyglycolethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxidecondensation products, alkyl polyethers, sorbitan esters, for examplesorbitan fatty acid esters or polyoxyethylene sorbitan esters, forexample polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active compound with finely dividedsolid substances, for example talc, natural clays, such as kaolin,bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be water- or oil-based. They can beprepared, for example, by wet milling using commercially customary beadmills, with or without the addition of surfactants as already mentionedabove, for example, in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared forexample by means of stirrers, colloid mills- and/or static mixers usingaqueous organic solvents and, if desired, surfactants as alreadymentioned above, for example, in the case of the other formulationtypes.

Granules can be prepared either by spraying the active compound ontoadsorptive, granulated inert material or by applying active-compoundconcentrates to the surface of carriers such as sand kaolinites orgranulated inert material, by means of adhesive binders, for examplepolyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitableactive compounds can also be granulated in the manner which is customaryfor the preparation of fertilizer granules, if desired as a mixture withfertilizers.

Water-dispersible granules are generally prepared by the customaryprocesses, such as spray-drying, fluidized-bed granulation, diskgranulation, mixing using high-speed mixers, and extrusion without solidinert material.

For the preparation of disk, fluidized-bed, extruder and spray granules,see for example processes in “Spray-Drying Handbook” 3rd ed. 1979, G.Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical andEngineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”,5th ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details on the formulation of crop protection products, seefor example G. C. Klingman, ‘Weed Control as a Science’, John Wiley andSons., Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans,“Weed Control Handbook”, 5th ed., Blackwell Scientific Publications,Oxford, 1968, pages 101-103.

The agrochemical formulations generally contain from 0.1 to 0.99% byweight, in particular from 0.1 to 95% by weight, of active compound ofthe formula (I).

In wettable powders the concentration of active compound is, forexample, from about 10 to 90% by weight, the remainder to 100% by weightconsisting of customary formulation constituents. In emulsifiableconcentrates the concentration of active compound can be from about 1 to90%, preferably from 5 to 80%, by weight. Formulations in the form ofdusts contain from 1 to 30% by weight of active compound, preferablymost commonly from 5 to 20% by weight of active compound, whilesprayable solutions contain from about 0.05 to 80%, preferably from 2 to50%, by weight of active compound. In the case of water-dispersiblegranules, the content of active compound depends partly on whether theactive compound, is in liquid or solid form and on the granulationauxiliaries, fillers, etc. that are used. In water-dispersible granulesthe content of active compound, for example, is between 1 and 95% byweight, preferably between 10 and 80% by weight.

In addition, said formulations of active compound may comprise thetackifiers, wetting agents, dispersants, emulsifiers, penetrants,preservatives, antifreeze agents, solvents, fillers, carriers,colorants, antifoams, evaporation inhibitors and pH and viscosityregulators which are customary in each case.

Suitable active compounds which can be combined with the activecompounds according to the invention in mixed formulations or in a tankmix are, for example, known active compounds, whose effect is based onan inhibition of, for example, acetolactate synthase, acetyl-CoAcarboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphatesynthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase,phytoene desaturase, photosystem I, photosystem II, protbporphyninogenoxidase, as described, for example, in Weed Research 26, 441-445 (1986),or “The Pesticide Manual”, 11th edition, The British Crop ProtectionCouncil and the Royal Soc. of Chemistry, 1997 and in the literaturecited therein. For example, the following active compounds may bementioned as herbicides which are known and which can be combined withthe compounds of the formula (I) (note: the compounds are eitherreferred to by the “common name” in accordance with the InternationalOrganization for Standardization (ISO) or by the chemical names, ifappropriate together with a customary code number): acetochlor;acifluorfen(-sodium); aclonifen; AKH 7088, i.e.[[[1-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]aceticacid and its methyl ester; alachlor; alloxydim(-sodium); ametryn;amicarbazone; amidosulfuron; amitrol; AMS, i.e. ammonium sulfamate;anilofos; asulam; atrazine; azafenidin; azimsulfuron; aziprotryn;barban; BAS 516H, i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one;beflubutamide; benazolin(-ethyl); benfluralin; benfuresate;bensulfuron(-methyl); bensulide; bentazone; benzobicyclone; benzofenap;benzofluor; benzoylprop(-ethyl); benzthiazuron; bialaphos; bifenox;bispyribac(-sodium); bromacil; bromobutide; bromofenoxim; bromoxynil;bromuron; buminafos; busoxinone; butachlor; butafenacil; butamifos;butenachlor; buthidazole; butralin; butroxydim; butylate; cafenstrole;caloxydim; carbetamide; cafentrazone(-ethyl); CDAA, i.e.2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chloroallyldiethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl;chlorbromuron; chlorbufam; chlorfenac; chlorflurecol-methyl;chloridazon; chlorimuron(-ethyl); chlormesulan (ICI-A0051);chlornitrofen; chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron;chlorthal(-dimethyl); chlorthiamid; cinidon(-ethyl and -methyl);cinmethylin; cinosulfuron; clefoxydim, clethodim; clodinafop and itsester derivatives (for example clodinafop-propargyl); clomazone;clomeprop; cloproxydim; clopyralid; clopyrasulfuron(-methyl);cloransulam(-methyl); cumyluron; cyanazine; cycloate; cyclosulfamuron;cycloxydim; cycluron; cyhalofop and its ester derivatives (for examplecyhalofop-butyl); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D;2,4-DB; dalapon; desmedipham; desmetryn; di-allate; dicamba;dichlobenil; dichlorprop; diclofop and its esters such asdiclofop-methyl; didosulam, i.e.N-(2,6-dichlorophenyl)-5-ethoxy-7-fluoro-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide;diethatyl(-ethyl); difenoxuron; difenzoquat; diflufenican;diflufenzopyr(-sodium); dimefuron; dimepiperate; dimethachlor;dimethametryn; dimethenamid; dimidazon; dimethipin; dinitramine;dinoseb; dinoterb; diphenamid; dipropetryn; diquat; dithiopyr; diuron;DNOC; eglinazine-ethyl; EL 77, i.e.5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide;endothal; EPTC; esprocarb; ethalfluralin; ethametsulfuron(-methyl);ethidimuron; ethiozin; ethofumesate; ethoxyfen and its esters (forexample ethyl acetate, HN-252); ethoxysulfuron; etobenzamid; F5231, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]ethanesulfonamide;fenoprop; fenoxan, fenoxaprop and fenoxaprop-P and their esters, forexample fenoxaprop-P-ethyl and fenoxaprop-ethyl, fenoxydim;fentrazamide; fenuron; flamprop(-methyl or -isopropyl or -isopropyl-L);flazasulfuron; florasulam; fluazifop and fluazifop-P and their esters(for example fluazifop-butyl and fluazifop-P-butyl);fluazolate(-isopropazol); flucarbazone(-sodium); fluchloralin;flufenacet; flumetsulam; flumeturon; flumiclorac and its esters (forexample flumiclorac-pentyl); flumioxazin; flurmipropyn; fluometuron;flupoxam (KNW-739); fluorodifen; fluoroglycofen(-ethyl); flupropacilflupyrsulfuron(-methyl, -sodium); flurenol (-butyl); fluridone;flurochloridone; fluroxypyr(-meptyl); flurtamone; fluthiacet(-methyl);fluthiamide; fomesafen; foramsulfuron; fosamine; furyloxyfen;glufosinate(-ammonium); glyphosate(-isopropylammonium); halosafen;halosulfuron(-methyl); haloxyfop and its esters; haloxyfop-P(═R-haloxyfop) and its esters; hexazinone; imazamethabenz; imazamox;imazapic; imazapyr; imazaquin(-ammonium); imazethamethapyr; imazethapyr;imazosulfuron; iridanofan; iodosulfuron; ioxynil; isocarbamid;isopropalin; isoproturon; isouron; isoxaben; isoxachlortole;isoxaflutole; isoxapyrifop; karbutilate; lactofen; lenacil; linuron;MCPA; MCPB; mecoprop; mefenacet; mefluidid; mesotrione; metarmitron;metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone;methyldymron; metobenzuron; metobromuron; (alpha-)metolachlor;metosulam; metoxuron; metribuzin; metsulfuron(-methyl); MH; molinate;monalide; monocarbamide dihydrogensulfate; monolinuron; monuron; MT 128,i.e.6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT5950, i.e. N-[3-chloro-4-(1-methylethyl)-phenyl]-2-methylpentanamide;naproanilide; napropamide; naptalam; NC 310, i.e.4-(2,4-dichlorobenzoyly)-1-methyl-5-benzyloxypyrazole; neburon;nicosulfuron; nipyraclophen; nitralin; nitrofen; nitrofluorfen;norflurazon; orbencarb; oryzalin; oxaciclomefone; oxadiargyl;oxadiazone; oxasulfuron; oxyfluorfen; paraquat; pebulate; pelargonicacid; pendimethalin; pentoxazone; perfluidone; phenisopham;phenmedipham; picloram; picolinafen; piperophos; piributicarb;pirifenop(-butyl); pretilachlor; primisulfuron(-methyl);procarbazone(-sodium); procyazine; prodiamine; profluralin;proglinazine(-ethyl); prometon; prometryn; propachlor; propanil;propaquizafop and its esters; propazine; propham; propisochlor;propyzamide; prosulfalin; prosulfocarb; prosulfuron; prynachlor;pyroflufen (-ethyl); pyrazolinate; pyrazon; pyrazosulfuron(-ethyl);pyrazoxyfen; pyribenzoxim; pyributicarb; pyridafol; pyridate;pyriminobac(-methyl); pyrithiobac(-sodium); pyroxofop and its esters(for example pyroxofop-propargyl); quinclorac, quinmerac; quinofop andits ester derivatives, quinodamine; quizalofop and quizalofop-P andtheir ester derivatives, (for example quizalofop-ethyl;quizalofop-P-tefuryl and ethyl); renriduron; rimsulfuron; S 275, i.e.2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazole;secbumeton; sethoxydim; siduron; simazine; simetryn; SN 106279, i.e.2-[[-[2-chloro-4-(trifluoromethyl)phenoxy]2-naphthalenyl]-oxy]propanoicacid and its methyl ester; sulcotrione; sulfentrazone; sulfazurone;sulfometuron(-methyl); sulfosate (ICI-A0224); sulfosulfuron;TCA(-sodium); tebutam; tebuthiuron; tepraloxydim; terbacil; terbucarb;terbuchlor; terbumeton; terbuthylazine, terbutryn, TFH 450, i.e.N,N-diethyl-3[(2-ethyl-6-methylphenyl)sulfonyl]1H-1,2,4-triazole-1-carboxamide;thenylchlor; thiafluamide; thiazafluron; thiazopyr; thidiazimin(SN-24085); thifensulfuron(-methyl); thiobencarb; tiocarbazil;tralkoxydim; tri-allate; triasulfuron; triaziflam; triazofenamide;tribenuron(-methyl); tridopyr; tridiphane; trietazine; trifluralin;triflusulfuron(-methyl); tritosulfuron; trimeturon; tsitodef; vernolate;WL 110547, i.e. 5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole;AMS-13668; D489; BH-60229; BH-71712, DK-8910; DOWCO-535; DPX-N8189;JTC-101; KH-218; KPP-300; KPP-421; LS 82-556; MBH-001; MT-146; MT;-147;NC-324; NC-330; OK-9403; OK-9604; OK-9701; PP-600; SC-0774 and UBH-509.

The active compounds according to the invention can also be used incombination with one or more compounds which act as safeners. Examplesof safeners are:

-   a) Compounds of the formulae (XIII) to (XV),    where the symbols and indices are as defined below:-   n′ is a natural number from 0 to 5, preferably from 0 to 3;-   T is a (C₁ or C₂)alkanediyl chain which is unsubstituted or    substituted by one or two (C₁-C₄)alkyl radicals or by    [(C₁-C₃)alkoxy]carbonyl;-   W⁺ is an unsubstituted or substituted divalent heterocyclic radical    selected from the group consisting of the partially unsaturated or    aromatic five-membered heterocycles having 1 to 3 hetero ring atoms    of the type N or O, where at least one nitrogen atom and at most one    oxygen atom is contained in the ring, preferably a radical from the    group (W⁺1) to (W⁺4);-   m′ is 0 or 1;-   R¹⁷, R¹⁹ are identical or different and are hydrogen, halogen,    (C₁-C₄)alkyl, (C₁-C₄)alkoxy, nitro or (C₁-C₄)haloalkyl;-   R¹⁸, R²⁰ are identical or different and are OR²⁴, SR²⁴ or NR²⁴R²⁵ or    a saturated or unsaturated 3- to 7-membered heterocycle having at    least one nitrogen atom and up to 3 heteroatoms, preferably selected    from the group consisting of O and S, which is attached via the    nitrogen atom with the carbonyl group in (XIII) or (XIV) and which    is unsubstituted or substituted by radicals selected from the group    consisting of (C₁-C₄)alkyl, (C₁-C₄)alkoxy or unsubstituted or    substituted phenyl, preferably a radical of the formula OR²⁴, NHR²⁵    or N(CH₃)₂, in particular of the formula OR²⁴;-   R²⁴ is hydrogen or an unsubstituted or substituted aliphatic    hydrocarbon radical, preferably having a total of from 1 to 18    carbon atoms;-   R²⁵ is hydrogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy or substituted or    unsubstituted phenyl;-   R²⁶ is hydrogen, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,    (C₁-C₄)alkoxy-(C₁-C₄)alkyl, (C₁-C₆)hydroxyalkyl, (C₃-C₁₂)cycloalkyl    or tri-(C₁-C₄)alkylsilyl;-   R²⁷, R²⁸, R²⁹ are identical or different and are hydrogen,    (C₁-C₈)alkyl, (C₁-C₈)haloalkyl, (C₃-C₁₂)cycloalkyl or substituted or    unsubstituted phenyl;-   R²¹ is (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₂-C₄)alkenyl,    (C₂-C₄)haloalkenyl, (C₃-C₇)cycloalkyl, preferably dichloromethyl:-   R²², R²³ are identical or different and are hydrogen, (C₁-C₄)alkyl,    (C₂-C₄)alkenyl, (C₂-C₄)alkynyl, (C₁-C₄)haloalkyl,    (C₂-C₄)haloalkenyl, (C₁-C₄)alkylcarbamoyl(C₁-C₄)alkyl,    (C₂-C₄)alkenylcarbamoyl(C₁-C₄)alkyl, (C₁-C₄)alkoxy(C₁-C₄)alkyl,    dioxolanyl-(C₁-C₄)alkyl, thiazolyl, furyl, furylalkyl, thienyl,    piperidyl, substituted or unsubstituted phenyl, or R²² and R²³    together form a substituted or unsubstituted heterocyclic ring,    preferably an oxazolidine, thiazolidine, piperidine, morpholine,    dihydropyrimidine or benzoxazine ring; or-   b) one or more compounds selected from the group consisting of:-   1,8-naphthalic anhydride,-   methyl diphenylmethoxyacetate,-   cyanomethoxyimino(phenyl)acetonitrile (cyQmetrinil),-   1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil),-   4′-chloro-2,2,2-trifluoroacetophenone 0-1,3-dioxolan-2-ylmethyloxime    (fluxofeninm),-   4,6-dichloro-2-phenylpyrimidine (fenclorim),-   benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate    (flurazole),-   2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191),-   N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (dymron),-   1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,-   1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,-   1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,-   1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea,-   (2,4-dichlorophenoxy)acetic acid (2,4-D),-   (4-chlorophenoxy)acetic acid,-   (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),-   4-(2,4-dichloropheinoxy)butyric acid (2,4-D B),-   (4-chloro-o-tolyloxy)acetic acid (MG PA),-   4-(4-chloro-o-tolyloxy)butyric acid,-   4-(4-chlorophenoxy)butyric acid,-   3,6-dichloro-2-methoxybenzoic acid (dicamba),-   1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate    (lactidichlor)-   and their salts and esters, preferably (C₁-C₈) esters;-   c) N-acylsulfonamides of the formula (XVI) and their salts    in which-   R³⁰ is hydrogen, a hydrocarbon radical, a hydrocarbon-oxy radical, a    hydrocarbon-thio radical or a heterocyclyl radical, each of the 4    last-mentioned radicals being unsubstituted or being substituted by    one or more identical or different radicals selected from the group    consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl,    formyl, carboxamide, sulfonamide and radicals of the formula    Z^(a)-R^(a),    -   each hydrocarbon moiety Preferably having 1 to 20 carbon atoms        and a carbon-containing radical R³⁰ inclusive of substituents        preferably having 1 to 30 carbon atoms;-   R³¹ is hydrogen or (C₁-C₄)alkyl, preferably hydrogen, or-   R³⁰ and R³¹ together with the group of the formula —CO—N— are the    radical of a 3- to 8-membered saturated or unsaturated ring;-   R³² is identical or different halogen, cyano, nitro, amino,    hydroxyl, carboxyl, formyl, CONH₂, SO₂NH₂ or a radical of the    formula Z^(b)-R^(b);-   R³³ is hydrogen or (C₁-C₄)alkyl, preferably H;-   R³⁴ is identical or different to halogen, cyano, nitro, amino,    hydroxyl, carboxyl, CHO, CONH₂, SO₂NH₂ or a radical of the formula.    Z^(c)-R^(c);-   R^(a) is a hydrocarbon radical or a heterocyclyl radical, each of    the two last-mentioned radicals being unsubstituted or substituted    by one or more identical or different radicals selected from the    group consisting of halogen, cyano, nitro, amino, hydroxyl, mono-    and di-[(C₁-C₄)alkyl]amino, or an alkyl radical in which a    plurality, preferably 2 or 3, non-adjacent CH₂ groups are in each    case replaced by one oxygen atom;-   R^(b),R^(c) are identical or different and are a hydrocarbon radical    or a heterocyclyl radical, each of the two last-mentioned radicals    being unsubstituted or substituted by one or more identical or    different radicals selected from the group consisting of halogen,    cyano, nitro, amino, hydroxyl, phosphoryl, halo(C₁-C₄)alkoxy, mono-    and di-[(C₁-C₄)alkyl]amino, or an alkyl radical in which a    plurality, preferably 2 or 3, non-adjacent CH₂ groups are replaced    in each case by one oxygen atom;-   Z^(a) is a divalent group of the formula —O—, —S—, —CO—, —CS—,    —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO₂—, —NR⁺—, —CO—NR⁺—,    —NR⁺—CO—, —SO₂—NR⁺— or —NR⁺—SO₂—, the bond given on the right-hand    side of each of the divalent groups being the bond to the radical    R^(a), and the radicals R⁺ in the 5 last-mentioned radicals    independently of each other being in each case H, (C₁-C₄)alkyl or    halo(C₁-C₄)alkyl;-   Z^(b),Z^(c) independently of one another are a direct bond or a    divalent group of the formula —O—, —S—, —CO—, —CS—, —CO—O—, —CO—S—,    —O—CO—, —S—CO—, —SO—, —S₂—, —NR⁺—, —SO₂—NR⁺—, —NR⁺—SO₂—, —CO—NR⁺— or    —NR⁺—CO—, the bond given on the right-hand side of each of the    divalent groups being the bond to the radical R^(b) or R^(c) and    where the radicals R⁺ in the 5 last-mentioned radicals independently    of one another are in each case. H, (C₁-C₄)alkyl or    halo(C₁-C₄)alkyl;-   n is an integer from 0 to 4, preferably 0, 1 or 2, in particular 0    or 1, and-   m is an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular    0, 1 or 2;-   d) acylsulfamoylbenzamides of the formula (XVII), optionally also in    salt form,    in which-   X³ is CH or N;-   R³⁵ is hydrogen, heterocyclyl or a hydrocarbon radical, the two    last-mentioned radicals optionally being substituted by one or more    identical or different radicals selected from the group consisting    of halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH₂,    SO₂NH₂ and Z^(a)-R^(a);-   R³⁶ is hydrogen, hydroxyl, (C₁-C₆)alkyl, (C₂-C₆)alkenyl,    (C₂-C₆)alkynyl, (C₁-C₆)alkoxy, (C₂-C₆)alkenyloxy, the five    last-mentioned radicals optionally being substituted by one or more    identical or different radicals selected from the group consisting    of halogen, hydroxyl, (C₁-C₄)alkyl, (C₁-C₄)alkoxy and    (C₁-C₄)alkylthio, or-   R³⁵ and R³⁶ together with the nitrogen atom to which they are    attached are a 3- to 8-membered saturated or unsaturated ring;-   R³⁷ is halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH₂,    SO₂NH₂ or Z^(b)-R^(b);-   R³⁸ is hydrogen, (C₁-C₄)alkyl, (C₂-C₄)alkenyl or (C₂-C₄)alkynyl;-   R³⁹ is halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl,    CHO, CONH₂, SO₂NH₂ or Z^(c)-R^(c);-   R^(d) is a (C₂-C₂₀)alkyl radical whose carbon chain is interrupted    once or more than once by oxygen atoms, or is heterocyclyl or a    hydrocarbon radical, the two last-mentioned radicals optionally    being substituted by one or more identical or different radicals    selected from the group consisting of halogen, cyano, nitro, amino,    hydroxyl, mono- and di-[(C₁-C₄)alkyl]amino;-   R^(b), R^(c) are identical or different and are a (C₂-C₂₀)alkyl    radical whose carbon chain is interrupted once or more than once by    oxygen atoms, or a heterocyclyl or a hydrocarbon radical, the two    last-mentioned radicals optionally being substituted by one or more    identical or different radicals selected from the group consisting    of halogen, cyano, nitro, amino, hydroxyl, phosphoryl,    (C₁-C₄)-haloalkoxy, mono- and di-[(C₁-C₄)alkyl]amino;-   Z^(a) is a divalent unit selected from the group consisting of O, S,    CO, CS, C(O)O, C(O)S, SO, SO₂, NR^(d), C(O)NR^(d) or SO₂NR^(d);-   Z^(b),Z^(c) are identical or different and are a direct bond or a    divalent unit selected from the group consisting of O, S, CO, CS,    C(O)O, C(O)S, SO, SO₂, NR^(d), SO₂NR^(d) or C(O)NR^(d);-   R^(d) is hydrogen, (C₁-C₄)alkyl or (C₁-C₄)haloalkyl;-   n is an integer from 0 to 4, and-   m in the event that X is CH, is an integer from 0 to 5 and, in the    event that X is N, is an integer from 0 to 4;-   e) compounds of the formula (XVIII),    in which the symbols and indices have the following meanings:-   R⁴⁰ is H, (C₁-C₄)alkyl, (C₁-C₄)alkyl substituted by (C₁-C₄)alkyl-X⁴    or (C₁-C₄)haloalkyl-X⁴, (C₁-C₄)haloalkyl, NO₂, CN, —COO—R⁴³, NR₂ ⁴⁴,    SO₂NR₂ ⁴⁵ or CONR₂ ⁴⁶;-   R⁴¹ is H, halogen, (C₁-C₄)alkyl, CF₃, (C₁-C₄)alkoxy or    (C₁-C₄)-haloalkoxy;-   R⁴² is H, halogen or (C₁-C₄)alkyl;-   Q¹, Q², E, G are identical or different, —O—, —S—, —CR₂ ⁴⁷—, —CO—,    —NR⁴⁸— or a group of the formula (XIX),    -   with the proviso that-   a) at least one of the groups Q¹, Q², E, G is a carbonyl group, that    exactly one of these groups is a radical of the formula (XIX) and    that the group of the formula (XIX) is adjacent to a carbonyl group,    and-   b) two adjacent groups Q¹, Q², E and G cannot simultaneously be    oxygen;-   R^(a) is identical or different H or (C₁-C₈)alkyl or the two    radicals R⁹ together are (C₂-C₆)alkylene;-   A is R^(b)—Y³— or —NR₂ ⁴⁹;-   X⁴ is —O— or —S(O)_(p)—;-   Y³ is —O— or —S—;-   R^(b) is H, (C₁-C₈)alkyl, (C₁-C₈)haloalkyl,    (C₁-C₄)alkoxy(C₁-C₈)alkyl, (C₃-C₆)alkenyloxy(C₁-C₈)alkyl, or    phenyl(C₁-C₈)alkyl, where the phenyl ring is optionally substituted    by halogen, (C₁-C₄)alkyl, CF₃, methoxy or methyl-S(O)_(p);    (C₃-C₆)alkenyl, (C₃-C₆)haloalkenyl, phenyl(C₃-C₆)alkenyl,    (C₃-C₆)alkynyl, phenyl(C₃-C₆)alkynyl, oxetanyl, furfuryl,    tetrahydrofuryl;-   R⁴³ is H or (C₁-C₄)alkyl;-   R⁴⁴ is identical or different H, (C₁-C₄)alkyl, (C₁-C₄)alkylcarbonyl    or the two radicals R⁴⁴ together are (C₄-C₅)alkylene;-   R⁴⁵, R⁴⁶ independently of one another are in each case identical or    different H, (C₁-C₄)alkyl, or the two radicals R⁴⁵ and/or R⁴⁶    together are (C₄-C₅)alkylene, where one CH₂ group can be replaced by    O or S or one or two CH₂ groups can be replaced by —NR^(c)—;-   R^(c) is H or (C₁-C₈)alkyl;-   R⁴⁷ is identical or different H, (C₁-C₈)alkyl or the two radicals    R⁴⁷ together are (C₂-C₆)alkylene;-   R⁴⁸ is —H, (C₁-C₈)alkyl, substituted or unsubstituted phenyl, or    benzyl which is unsubstituted or substituted on the phenyl ring;-   R⁴⁹ is identical or different H, (C₁-C₈)alkyl, phenyl,    phenyl(C₁-C₈)alkyl, where a phenyl ring can be substituted by F, Cl,    Br, NO₂, CN, OCH₃, (C₁-C₄)alkyl or CH₃SO₂—;    (C₁-C₄)alkoxy(C₁-C₈)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl,    (C₃-C₆)cycloalkyl or two radicals R⁴⁹ together are (C₄-C₅)alkylene,    where one CH₂ group can be replaced: by O or S or one or two CH₂    groups can be replaced by —NR^(d)—;-   R^(d) is H or (C₁-C₄)alkyl;-   m″ is 0 or 1 and-   p is 0, 1 or 2;    inclusive of the stereoisomers and the agriculturally customary    salts.

For use, the formulations which are present in commercially availableform are, if appropriate, diluted in the customary manner, for exampleusing water in the case of wettable powders, emulsifiable concentrates,dispersions and water-dispersible granules. Preparations in the form ofdusts, granules for soil application or broadcasting and sprayablesolutions are usually not further diluted with other inert substancesprior to use.

The application rate of the compounds of the formula (I) required varieswith the external conditions, such as temperature, humidity, the natureof the herbicide used and the like. It can vary within wide limits, forexample between 0.001 and 10.0 kg/ha or more of active substance, but itis preferably between 0.005 and 5 kg/ha.

EXAMPLES A. Chemical Examples Example A1 Methyl2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate

At 0° C., 1.4 ml (13.3 mmol) of tert-butylamine are added dropwise to asolution of 1.00 g (3.58 mmol) ofmethyl-2-(chlorosulfonyl)-6-nitrobenzoate in 8 ml of dichloromethane,and the reaction mixture is then allowed to warm to room temperature.After 2 h, the reaction mixture is poured into ice-water, adjusted to pH3 using 2 N aqueous hydrochloric acid and extracted withdichloromethane. The organic phase is then dried over sodium sulfate,filtered off and concentrated to dryness under reduced pressure. Theresidue that remains is digested with diethyl ether and filtered offwith suction. This gives 1.06 g (91% of theory) of methyl2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate of m.p. 89-91° C.

Example A2 Methyl 2-(aminosulfonyl)-6-nitrobenzoate

300 mg (0.948 mmol) of methyl2-[(tert-butylamino)sulfonyl]-6-nitrobenzoate in 8 ml of trifluoroaceticacid are stirred at room temperature for 4 h. The mixture issubsequently concentrated to dryness under reduced pressure and theresidue is digested with diethyl ether. After filtration with suctionand drying, 230 mg (93% of theory) of methyl2-(aminosulfonyl)-6-nitrobenzoate of m.p. 227-229° C. remain.

Example A3 Methyl2-[(tert-butylamino)sulfonyl]-6-(isopropylamino)benzoate

At a temperature of 5-10° C., 925 mg (24.4 mmol) of sodium borohydrideare stirred into 14 ml of acetic acid. After 1 h, this mixture isadmixed first with 1.42 g (24.4 mmol) of acetone and then with 700 mg(2.44 mmol) of methyl 2-amino-6-[(tert-butylamino)sulfonyl]benzoate andstirred at 5-10° C. for 2.5 h. For work-up, the reaction mixture ispoured into ice-water, neutralized with aqueous ammonia solution andextracted with dichloromethane. The organic phase is concentrated andthe residue that remains is triturated with diisopropyl ether. Afterfiltration with suction and drying, 700 mg (89% of theory) of methyl2-[(tert-butylamino)sulfonyl]-6-(isopropylamino)benzoate remain as awhite solid of m.p. 110′-112° C.

Example A4 Methyl 2-amino-6-[(tert-butylamino)sulfonyl]benzoate

A solution of 8.00 g (25.3 mmol) of methyl2-[(tert-butylaminoysulfonyl]-6-nitrobenzoate is admixed with 3.2 g ofpalladium on activated carbon (5%) and hydrogenated at room temperatureand under atmospheric pressure for 6 h. The reaction mixture is thenfiltered, the filtrate is concentrated to dryness and the residue ispurified by silica gel chromatography [TLC (SiO₂) ethylacetate/n-heptane 1:1; R_(f)=0.38] using ethyl acetate/n-heptane (1:1).Evaporation gives 6.23 g (86% of theory) of methyl2-amino-6-[(tert-butylamino)sulfonyl]benzoate as a beige solid ofmelting point 132-133° C.

Example A5 Methyl2-(diisobutylamino)-6-[([(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl-amino)sulfonyl]benzoate

700 mg (2.04 mmol) of methyl2-(diisobutylamino)-6-(sulfonylamino)benzoate and 619 mg (2.25 mmol) ofphenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate are initially charged in10 ml of acetonitrile. At room temperature, '375 mg (2.51 mmol) of1,8-diazabicyclo[5.4.0]undec-7-ene (1,5-5) (DBU) are then addeddropwise, and the reaction mixture is stirred at this temperature for 3h. The mixture is then poured into ice-water and the solution is slowlyadjusted to pH 1 using 2. N hydrochloric acid. The precipitated solid isfiltered off with suction, washed with water and dried. This gives 910mg (91% of theory) of methyl2-(diisobutylamino)-6-[([(4,6-dimethoxy-2-pyrimidinyl)amino]carbonylamino)sulfonyl]benzoateof m.p. 166-167° C.

Example A6 Methyl2-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonylamino)sulfonyl]-6-nitrobenzoate

At 55-60° C. and under argon, a solution of 5.0 g (17.9 mmol) of methyl2-chlorosulfonyl-6-nitrobenzobate in 55 ml of dry dichloromethane isadded dropwise over 2 h to a suspension of 2.79 g (17.9 mmol) of2-amino-4,6-dimethoxy-1,3,5-triazine, 1.28 g (19.7 mmol) of sodiumcyanate, 1.45 ml (17.9 mmol) of pyridine and 500 mg of freshly activatedmolecular sieve (pore size 3 Å) in 85 ml of dry acetonitrile. After 7 hof stirring at this temperature, the mixture is allowed to warm to roomtemperature. After a further 12 h, the reaction mixture is, concentratedand the residue is suspended in 200 ml of water and adjusted to pH 10using 2 N aqueous sodium hydroxide solution. The precipitated solid isfiltered off with suction and the filtrate is extracted with ethylacetate. The organic phase is separated off and the aqueous phase isadjusted to pH 1.5 using 3 N aqueous hydrochloric acid solution andstirred in an ice bath for 15 min. The precipitated solid is thenfiltered off with suction, washed first with water and then withmethanol and dried under reduced pressure. This gives 2.88 g (36% oftheory) of methyl2-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonylamino)sulfonyl]-6-nitrobenzoateof m.p. 185-195° C. (decomp.).

Example A7 Methyl2-amino-6-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonylamino)-sulfonyl]benzoate

50 mg (113 μmol) of methyl2-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]-carbonylamino)sulfonyl]-6-nitrobenzoateare suspended in a mixture of 3 ml of methanol/dimethylformamide (5:1),admixed with 10 mg. of palladium on activated carbon (5%) and 1 mg (8.20μmol) of sodium (meta)vanadate and, hydrogenated under atmosphericpressure and at room temperature for 3 h. The mixture is then filteredoff, the filtrate is concentrated and the residue is taken up in waterand adjusted to pH 1.5 using 3 N aqueous hydrochloric acid solution. Theprecipitate is stirred in an ice-bath for 10 min and then filtered offwith suction and dried under reduced pressure. This gives 41 mg (87% oftheory) of methyl2-amino-6-[([(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]carbonylamino)sulfonyl]benzoateof m.p. 129-134° C. (decomp.).

Example A8 Methyl2-(diisobutylamino)-6-[([(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl-amino)sulfonyl]benzoate,sodium salt

0.2 g (0.382 mmol) of methyl2-(diisobutylamino)-6-[([(4,6-dimethoxy-2-pyrimidinyl)amino]carbonylamino)sulfonyl]benzoateare stirred into 5 ml of tetrahydrofuran, and 0.04 g (416 μmol) ofsodium tert-butoxide are then added. After 6 h, the solid that has beenformed is filtered off with suction and dried. This gives 0.19 g (93% oftheory) of methyl2-(diisobutylamino)-6-[([(4,6-dimethoxy-2-pyrimidinyl)amino]carbonylamino)-6-sulfonyl]benzoate,sodium salt, as a colorless solid of m.p. 215-217° C.

The compounds described in Tables 1, 2 and 3 below are obtained inaccordance with or similarly to Examples A1-A8 above.

Abbreviations in Tables 1, 2 and 3: m.p. = melting point in ° C.(decomp.) = melting point with decomposition Bu = n-butyl;(correspondingly pentyl = n-pentyl, hexyl = n-hexyl) Et = ethyl Me =methyl Ph = phenyl Pr, i-Pr, c-Pr = n-propyl, isopropyl and cyclopropyl,respectively

A diradical such as butylene of the formula

in the columns for R², R³ means that R² and R³ together are thediradical bridge and form a cyclic amine together with the nitrogen atomof the group R²R³N.

Het=heterocycle, where Het is one of the radicals T1 to T20

TABLE 1 Compounds of the formula (Ia) (Ia)

Ex. No. R¹ R² R³ R⁴ R⁵ M Het m.p. 1-1. H H H — H H T1 1-2. H H H — H NaT1 1-3. H H H — H H T2 1-4. H H H — H Na T2 1-5. H H H — H H T5 1-6. H HH — H Na T5 1-7. H H H — H H T6 1-8. H H H — H Na T6 1-9. H H H — H H T7141-142 1-10. H H H — H Na T7 1-11. Me H H — H H T1 171-173 1-12. Me H H— H Na T1 1-13. Me H H — Me H T2 1-14. Me H H — Me Na T2 1-15. Me H H —H H T2 126-127 (decomp.) 1-16. Me H H — H Na T2 239-242 1-17. Me H H — HH T3 137-139 (decomp.) 1-18. Me H H — H Na T3 1-19. Me H H — H H T41-20. Me H H — H Na T4 1-21. Me H H — H H T5 1-22. Me H H — H Na T51-23. Me H H — H H T6 137-139 1-24. Me H H — H Na T6 1-25. Me H H — H HT7 129-134 (decomp.) 1-26. Me H H — H Na T7 257-260 (decomp.) 1-27. Me HH — Me H T7 1-28. Me H H — Me Na T7 1-29. Me H H — H H T8 1-30. Me H H —H Na T8 1-31. Me H H — H H T9 1-32. Me H H — H Na T9 1-33. Me H H — H HT10 1-34. Me H H — H Na T10 1-35. Me H H — H H T11 1-36. Me H H — H NaT11 1-37. Me H H — H H T12 1-38. Me H H — H Na T12 1-39. Me H H — H HT13 1-40. Me H H — H Na T13 1-41. Me H H — H H T14 162-164 (decomp.)1-42. Me H H — H Na T14 1-43. Me H H — H H T15 1-44. Me H H — H Na T151-45. Et H H — H H T1 164-166 1-46. Et H H — H Na T1 1-47. Et H H — H HT2 149-151 1-48. Et H H — H Na T2 1-49. Et H H — H H T3 1-50. Et H H — HNa T3 1-51. Et H H — H H T4 1-52. Et H H — H Na T4 1-53. Et H H — H H T51-54. Et H H — H Na T5 1-55. Et H H — H H T6 157-158 1-56. Et H H — H NaT6 1-57. Et H H — H H T7 158-160 1-58. Et H H — H Na T7 1-59. Et H H — HH T8 1-60. Et H H — H Na T8 1-61. Et H H — H H T9 1-62. Et H H — H Na T91-63. Et H H — H H T10 1-64. Et H H — H Na T10 1-65. Et H H — H H T111-66. Et H H — H Na T11 1-67. Et H H — H H T12 1-68. Et H H — H Na T121-69. Et H H — H H T13 1-70. Et H H — H Na T13 1-71. Et H H — H H T141-72. Et H H — H Na T14 1-73. Et H H — H H T15 1-74. Et H H — H Na T151-75. i-Pr H H — H H T1 1-76. i-Pr H H — H Na T1 1-77. i-Pr H H — H H T21-78. i-Pr H H — H Na T2 1-79. i-Pr H H — H H T5 1-80. i-Pr H H — H NaT5 1-81. i-Pr H H — H H T6 1-82. i-Pr H H — H Na T6 1-83. i-Pr H H — H HT7 1-84. i-Pr H H — H Na T7 1-85. Allyl H H — H H T1 1-86. Allyl H H — HNa T1 1-87. Allyl H H — H H T2 1-88. Allyl H H — H Na T2 1-89. Allyl H H— H H T5 1-90. Allyl H H — H Na T5 1-91. Allyl H H — H H T6 1-92. AllylH H — H Na T6 1-93. Allyl H H — H H T7 1-94. Allyl H H — H Na T7 1-95.3-Oxetanyl H H — H H T1 1-96. 3-Oxetanyl H H — H Na T1 1-97. 3-OxetanylH H — H H T2 1-98. 3-Oxetanyl H H — H Na T2 1-99. 3-Oxetanyl H H — H HT5 1-100. 3-Oxetanyl H H — H Na T5 1-101. 3-Oxetanyl H H — H H T6 1-102.3-Oxetanyl H H — H Na T6 1-103. 3-Oxetanyl H H — H H T7 1-104.3-Oxetanyl H H — H Na T7 1-105. Me Me H — H H T1 169-171 1-106. Me Me H— H Na T1 1-107. Me Me H — H H T2 1-108. Me Me H — H Na T2 1-109. Me MeH — H H T6 1-110. Me Me H — H Na T6 1-111. Me Me H — H H T7 1-112. Me MeH — H Na T7 1-113. Et Me H — H H T1 1-114. Et Me H — H Na T1 1-115. EtMe H — H H T2 1-116. Et Me H — H Na T2 1-117. i-Pr Me H — H H T1 1-118.i-Pr Me H — H Na T1 1-119. i-Pr Me H — H H T2 1-120. i-Pr Me H — H Na T21-121. Allyl Me H — H H T1 1-122. Allyl Me H — H Na T1 1-123. Allyl Me H— H H T2 1-124. Allyl Me H — H Na T2 1-125. 3-Oxetanyl Me H — H H T11-126. 3-Oxetanyl Me H — H Na T1 1-127. 3-Oxetanyl Me H — H H T2 1-128.3-Oxetanyl Me H — H Na T2 1-129. Me Et H — H H T1 164-166 1-130. Me Et H— H Na T1 1-131. Me Et H — H H T2 215-217 1-132. Me Et H — H Na T21-133. Me Et H — H H T6 1-134. Me Et H — H Na T6 1-135. Me Et H — H H T7170-172 1-136. Me Et H — H Na T7 1-137. Et Et H — H H T1 1-138. Et Et H— H Na T1 1-139. Et Et H — H H T2 1-140. Et Et H — H Na T2 1-141. i-PrEt H — H H T1 1-142. i-Pr Et H — H Na T1 1-143. i-Pr Et H — H H T21-144. i-Pr Et H — H Na T2 1-145. Allyl Et H — H H T1 1-146. Allyl Et H— H Na T1 1-147. Allyl Et H — H H T2 1-148. Allyl Et H — H Na T2 1-149.3-Oxetanyl Et H — H H T1 1-150. 3-Oxetanyl Et H — H Na T1 1-151.3-Oxetanyl Et H — H H T2 1-152. 3-Oxetanyl Et H — H Na T2 1-153. Me i-PrH — H H T1 165-167 1-154. Me i-Pr H — H Na T1 124-126 1-155. Me i-Pr H —H H T2 139-140 (decomp.) 1-156. Me i-Pr H — H Na T2 1-157. Me i-Pr H — HH T6 1-158. Me i-Pr H — H Na T6 1-159. Me i-Pr H — H H T7 161-163(decomp.) 1-160. Me i-Pr H — H Na T7 1-161. Et i-Pr H — H H T1 1-162. Eti-Pr H — H Na T1 1-163. Et i-Pr H — H H T2 1-164. Et i-Pr H — H Na T21-165. i-Pr i-Pr H — H H T1 1-166. i-Pr i-Pr H — H Na T1 1-167. i-Pri-Pr H — H H T2 1-168. i-Pr i-Pr H — H Na T2 1-169. Allyl i-Pr H — H HT1 1-170. Allyl i-Pr H — H Na T1 1-171. Allyl i-Pr H — H H T2 1-172.Allyl i-Pr H — H Na T2 1-173. 3-Oxetanyl i-Pr H — H H T1 1-174.3-Oxetanyl i-Pr H — H Na T1 1-175. 3-Oxetanyl i-Pr H — H H T2 1-176.3-Oxetanyl i-Pr H — H Na T2 1-177. Me CH₂i-Pr H — H H T1 163-165 1-178.Me CH₂i-Pr H — H Na T1 1-179. Me CH₂i-Pr H — H H T2 171-173 (decomp.)1-180. Me CH₂i-Pr H — H Na T2 1-181. Me CH₂i-Pr H — H H T6 1-182. MeCH₂i-Pr H — H Na T6 1-183. Me CH₂i-Pr H — H H T7 174-176 (decomp.)1-184. Me CH₂i-Pr H — H Na T7 1-185. Et CH₂i-Pr H — H H T1 1-186. EtCH₂i-Pr H — H Na T1 1-187. Et CH₂i-Pr H — H H T2 1-188. Et CH₂i-Pr H — HNa T2 1-189. Et CH₂i-Pr H — H H T6 1-190. Et CH₂i-Pr H — H Na T6 1-191.Et CH₂i-Pr H — H H T7 1-192. Et CH₂i-Pr H — H Na T7 1-193. i-Pr CH₂i-PrH — H H T1 1-194. i-Pr CH₂i-Pr H — H Na T1 1-195. i-Pr CH₂i-Pr H — H HT2 1-196. i-Pr CH₂i-Pr H — H Na T2 1-197. Allyl CH₂i-Pr H — H H T11-198. Allyl CH₂i-Pr H — H Na T1 1-199. Allyl CH₂i-Pr H — H H T2 1-200.Allyl CH₂i-Pr H — H Na T2 1-201. 3-Oxetanyl CH₂i-Pr H — H H T1 1-202.3-Oxetanyl CH₂i-Pr H — H Na T1 1-203. 3-Oxetanyl CH₂i-Pr H — H H T21-204. 3-Oxetanyl CH₂i-Pr H — H Na T2 1-205. Me CH₂CH₂F H — H H T11-206. Me CH₂CH₂F H — H Na T1 1-207. Me CH₂CH₂F H — H H T2 1-208. MeCH₂CH₂F H — H Na T2 1-209. Me CH₂CH₂F H — H H T6 1-210. Me CH₂CH₂F H — HNa T6 1-211. Me CH₂CH₂F H — H H T7 1-212. Me CH₂CH₂F H — H Na T7 1-213.Et CH₂CH₂F H — H H T1 1-214. Et CH₂CH₂F H — H Na T1 1-215. Et CH₂CH₂F H— H H T2 1-216. Et CH₂CH₂F H — H Na T2 1-217. Et CH₂CH₂F H — H H T61-218. Et CH₂CH₂F H — H Na T6 1-219. Et CH₂CH₂F H — H H T7 1-220. EtCH₂CH₂F H — H Na T7 1-221. i-Pr CH₂CH₂F H — H H T1 1-222. i-Pr CH₂CH₂F H— H Na T1 1-223. i-Pr CH₂CH₂F H — H H T2 1-224. i-Pr CH₂CH₂F H — H Na T21-225. Allyl CH₂CH₂F H — H H T1 1-226. Allyl CH₂CH₂F H — H Na T1 1-227.Allyl CH₂CH₂F H — H H T2 1-228. Allyl CH₂CH₂F H — H Na T2 1-229.3-Oxetanyl CH₂CH₂F H — H H T1 1-230. 3-Oxetanyl CH₂CH₂F H — H Na T11-231. 3-Oxetanyl CH₂CH₂F H — H H T2 1-232. 3-Oxetanyl CH₂CH₂F H — H NaT2 1-233. Me CH₂CH₂CF₃ H — H H T1 1-234. Me CH₂CH₂CF₃ H — H Na T1 1-235.Me CH₂CH₂CF₃ H — H H T2 1-236. Me CH₂CH₂CF₃ H — H Na T2 1-237. MeCH₂CH₂CF₃ H — H H T6 1-238. Me CH₂CH₂CF₃ H — H Na T6 1-239. Me CH₂CH₂CF₃H — H H T7 1-240. Me CH₂CH₂CF₃ H — H Na T7 1-241. Me CH₂CH₂CH₂CF₃ H — HH T1 173-175 1-242. Me CH₂CH₂CH₂CF₃ H — H Na T1 1-243. Me CH₂CH₂CH₂CF₃ H— H H T2 177-179 1-244. Me CH₂CH₂CH₂CF₃ H — H Na T2 1-245. MeCH₂CH₂CH₂CF₃ H — H H T6 1-246. Me CH₂CH₂CH₂CF₃ H — H Na T6 1-247. MeCH₂CH₂CH₂CF₃ H — H H T7 171-173 1-248. Me CH₂CH₂CH₂CF₃ H — H Na T71-249. Me CH(Me)CH₂C(O)OMe H — H H T1 1-250. Me CH(Me)CH₂C(O)OMe H — HNa T1 1-251. Me CH(Me)CH₂C(O)OMe H — H H T2 1-252. Me CH(Me)CH₂C(O)OMe H— H Na T2 1-253. Me CH(Me)CH₂C(O)OMe H — H H T6 1-254. MeCH(Me)CH₂C(O)OMe H — H Na T6 1-255. Me CH(Me)CH₂C(O)OMe H — H H T71-256. Me CH(Me)CH₂C(O)OMe H — H Na T7 1-257. Me CH(Me)CH₂C(O)NH₂ H — HH T1 1-258. Me CH(Me)CH₂C(O)NH₂ H — H Na T1 1-259. Me CH(Me)CH₂C(O)NH₂ H— H H T2 1-260. Me CH(Me)CH₂C(O)NH₂ H — H Na T2 1-261. MeCH(Me)CH₂C(O)NH₂ H — H H T6 1-262. Me CH(Me)CH₂C(O)NH₂ H — H Na T61-263. Me CH(Me)CH₂C(O)NH₂ H — H H T7 1-264. Me CH(Me)CH₂C(O)NH₂ H — HNa T7 1-265. Me CH(Me)CH₂CH₃ H — H H T1 171-173 1-266. Me CH(Me)CH₂CH₃ H— H Na T1 1-267. Me CH(Me)CH₂CH₃ H — H H T2 154-156 1-268. MeCH(Me)CH₂CH₃ H — H Na T2 1-269. Me CH(Me)CH₂CH₃ H — H H T6 1-270. MeCH(Me)CH₂CH₃ H — H Na T6 1-271. Me CH(Me)CH₂CH₃ H — H H T7 172-1741-272. Me CH(Me)CH₂CH₃ H — H Na T7 1-273. Me Allyl H — H H T1 1-274. MeAllyl H — H Na T1 1-275. Me Allyl H — H H T2 1-276. Me Allyl H — H Na T21-277. Me Allyl H — H H T6 1-278. Me Allyl H — H Na T6 1-279. Me Allyl H— H H T7 1-280. Me Allyl H — H Na T7 1-281. Et Allyl H — H H T1 1-282.Et Allyl H — H Na T1 1-283. Et Allyl H — H H T2 1-284. Et Allyl H — H NaT2 1-285. Et Allyl H — H H T6 1-286. Et Allyl H — H Na T6 1-287. EtAllyl H — H H T7 1-288. Et Allyl H — H Na T7 1-289. i-Pr Allyl H — H HT1 1-290. i-Pr Allyl H — H Na T1 1-291. i-Pr Allyl H — H H T2 1-292.i-Pr Allyl H — H Na T2 1-293. Allyl Allyl H — H H T1 1-294. Allyl AllylH — H Na T1 1-295. Allyl Allyl H — H H T2 1-296. Allyl Allyl H — H Na T21-297. 3-Oxetanyl Allyl H — H H T1 1-298. 3-Oxetanyl Allyl H — H Na T11-299. 3-Oxetanyl Allyl H — H H T2 1-300. 3-Oxetanyl Allyl H — H Na T21-301. Me Propargyl H — H H T1 1-302. Me Propargyl H — H Na T1 1-303. MePropargyl H — H H T2 1-304. Me Propargyl H — H Na T2 1-305. Me PropargylH — H H T6 1-306. Me Propargyl H — H Na T6 1-307. Me Propargyl H — H HT7 1-308. Me Propargyl H — H Na T7 1-309. Et Propargyl H — H H T1 1-310.Et Propargyl H — H Na T1 1-311. Et Propargyl H — H H T2 1-312. EtPropargyl H — H Na T2 1-313. Et Propargyl H — H H T6 1-314. Et PropargylH — H Na T6 1-315. Et Propargyl H — H H T7 1-316. Et Propargyl H — H NaT7 1-317. i-Pr Propargyl H — H H T1 1-318. i-Pr Propargyl H — H Na T11-319. i-Pr Propargyl H — H H T2 1-320. i-Pr Propargyl H — H Na T21-321. Allyl Propargyl H — H H T1 1-322. Allyl Propargyl H — H Na T11-323. Allyl Propargyl H — H H T2 1-324. Allyl Propargyl H — H Na T21-325. 3-Oxetanyl Propargyl H — H H T1 1-326. 3-Oxetanyl Propargyl H — HNa T1 1-327. 3-Oxetanyl Propargyl H — H H T2 1-328. 3-Oxetanyl PropargylH — H Na T2 1-329. Me OMe H — H H T1 1-330. Me OMe H — H Na T1 1-331. MeOMe H — H H T2 1-332. Me OMe H — H Na T2 1-333. Me OMe H — H H T6 1-334.Me OMe H — H Na T6 1-335. Me OMe H — H H T7 1-336. Me OMe H — H Na T71-337. Et OMe H — H H T1 1-338. Et OMe H — H Na T1 1-339. Et OMe H — H HT2 1-340. Et OMe H — H Na T2 1-341. Et OMe H — H H T6 1-342. Et OMe H —H Na T6 1-343. Et OMe H — H H T7 1-344. Et OMe H — H Na T7 1-345. i-PrOMe H — H H T1 1-346. i-Pr OMe H — H Na T1 1-347. i-Pr OMe H — H H T21-348. i-Pr OMe H — H Na T2 1-349. Allyl OMe H — H H T1 1-350. Allyl OMeH — H Na T1 1-351. Allyl OMe H — H H T2 1-352. Allyl OMe H — H Na T21-353. Me c-Pr H — H H T1 148-150 (decomp.) 1-354. Me c-Pr H — H Na T11-355. Me c-Pr H — H H T2 147-149 1-356. Me c-Pr H — H Na T2 1-357. Mec-Pr H — H H T6 1-358. Me c-Pr H — H Na T6 1-359. Me c-Pr H — H H T7177-179 1-360. Me c-Pr H — H Na T7 1-361. 3-Oxetanyl OMe H — H H T11-362. 3-Oxetanyl OMe H — H Na T1 1-363. 3-Oxetanyl OMe H — H H T21-364. 3-Oxetanyl OMe H — H Na T2 1-365. Me NMe₂ H — H H T1 1-366. MeNMe₂ H — H Na T1 1-367. Me NMe₂ H — H H T2 1-368. Me NMe₂ H — H Na T21-369. Me NHCHO H — H H T1 1-370. Me NHCHO H — H Na T1 1-371. Me NHCHO H— H H T2 1-372. Me NHCHO H — H Na T2 1-373. Me NHC(O)Me H — H H T11-374. Me NHC(O)Me H — H Na T1 1-375. Me NHC(O)Me H — H H T2 1-376. MeNHC(O)Me H — H Na T2 1-377. Me NHSO₂Me H — H H T1 1-378. Me NHSO₂Me H —H Na T1 1-379. Me NHSO₂Me H — H H T2 1-380. Me NHSO₂Me H — H Na T21-381. Me CH₂Ph H — H H T1 189-191 1-382. Me CH₂Ph H — H Na T1 1-383. MeCH₂Ph H — H H T2 151-153 1-384. Me CH₂Ph H — H Na T2 1-385. Me CH₂Ph H —H H T6 1-386. Me CH₂Ph H — H Na T6 1-387. Me CH₂Ph H — H H T7 166-168(decomp.) 1-388. Me CH₂Ph H — H Na T7 1-389. Me CH₂OMe H — H H T1 1-390.Me CH₂OMe H — H Na T1 1-391. Me CH₂OMe H — H H T2 1-392. Me CH₂OMe H — HNa T2 1-393. Me CH₂C(O)Me H — H H T1 1-394. Me CH₂C(O)Me H — H Na T11-395. Me CH₂C(O)Me H — H H T2 1-396. Me CH₂C(O)Me H — H Na T2 1-397. MeCH₂C(O)OMe H — H H T1 1-398. Me CH₂C(O)OMe H — H Na T1 1-399. MeCH₂C(O)OMe H — H H T2 1-400. Me CH₂C(O)OMe H — H Na T2 1-401. Me Me Me —H H T1 194-196 1-402. Me Me Me — H Na T1 1-403. Me Me Me — H H T2 1-404.Me Me Me — H Na T2 1-405. Me Me Me — H H T6 1-406. Me Me Me — H Na T61-407. Me Me Me — H H T7 1-408. Me Me Me — H Na T7 1-409. Me Me Et — H HT1 1-410. Me Me Et — H Na T1 1-411. Me Me Et — H H T2 1-412. Me Me Et —H Na T2 1-413. Me Me i-Pr — H H T1 1-414. Me Me i-Pr — H Na T1 1-415. MeMe i-Pr — H H T2 1-416. Me Me i-Pr — H Na T2 1-417. Me Et Et — H H T1207-209 1-418. Me Et Et — H Na T1 1-419. Me Et Et — H H T2 1-420. Me EtEt — H Na T2 1-421. Me i-Pr i-Pr — H H T1 1-422. Me i-Pr i-Pr — H Na T11-423. Me i-Pr i-Pr — H H T2 1-424. Me i-Pr i-Pr — H Na T2 1-425. MeCH₂i-Pr CH₂i-Pr — H H T1 166-167 1-426. Me CH₂i-Pr CH₂i-Pr — H Na T1215-217 1-427. Me CH₂i-Pr CH₂i-Pr — H H T2 1-428. Me CH₂i-Pr CH₂i-Pr — HNa T2 1-429. Me

— H H T1 1-430. Me

— H Na T1 1-431. Me

— H H T2 1-432. Me

— H Na T2 1-433. Me

— H H T1 216-218 1-434. Me

— H Na T1 1-435. Me

— H H T2 193-195 1-436. Me

— H Na T2 1-437. Me

— H H T6 1-438. Me

— H Na T6 1-439. Me

— H H T7 200-202 1-440. Me

— H Na T7 1-441. Me

— H H T1 1-442. Me

— H Na T1 1-443. Me

— H H T2 1-444. Me

— H Na T2 1-445. Me

— H H T1 1-446. Me

— H Na T1 1-447. Me

— H H T2 1-448. Me

— H Na T2 1-449. Me

— H H T1 1-450. Me

— H Na T1 1-451. Me

— H H T2 1-452. Me

— H Na T2 1-453. Me

— H H T1 211-213 (decomp.) 1-454. Me

— H Na T1 1-455. Me

— H H T2 208-209 1-456. Me

— H Na T2 1-457. Me

— H H T6 1-458. Me

— H Na T6 1-459. Me

— H H T7 201-203 1-460. Me

— H Na T7 1-461. Me

— H H T1 1-462. Me

— H Na T1 1-463. Me

— H H T2 1-464. Me

— H Na T2 1-465. Me H H 5-Me H H T1 1-466. Me H H 5-Me H Na T1 1-467. MeH H 5-Me H H T2 1-468. Me H H 5-Me H Na T2 1-469. Me H H 5-F H H T11-470. Me H H 5-F H Na T1 1-471. Me H H 5-F H H T2 1-472. Me H H 5-F HNa T2 1-473. Me H H 5-Cl H H T1 1-474. Me H H 5-Cl H Na T1 1-475. Me H H5-Cl H H T2 1-476. Me H H 5-Cl H Na T2 1-477. Me H H 5-OMe H H T1 1-478.Me H H 5-OMe H Na T1 1-479. Me H H 5-OMe H H T2 1-480. Me H H 5-OMe H NaT2 1-481. Me H H 5-NO₂ H H T1 1-482. Me H H 5-NO₂ H Na T1 1-483. Me H H5-NO₂ H H T2 1-484. Me H H 5-NO₂ H Na T2 1-485. Me H H 6-Me H H T11-486. Me H H 6-Me H Na T1 1-487. Me H H 6-Me H H T2 1-488. Me H H 6-MeH Na T2 1-489. Me H H 6-Cl H H T1 1-490. Me H H 6-Cl H Na T1 1-491. Me HH 6-Cl H H T2 1-492. Me H H 6-Cl H Na T2

TABLE 2 Compounds of the formula (Ib) (Ib)

Ex. No. R¹ R* R² R³ R⁴ M Het m.p. 2-1. H H H H — H T1 2-2. H H H H — NaT1 2-3. H H H H — H T2 2-4. H H H H — Na T2 2-5. Me Me H H — H T1 2-6.Me Me H H — Na T1 2-7. Me Me H H — H T2 2-8. Me Me H H — Na T2 2-9. MeMe H H — H T5 2-10. Me Me H H — Na T5 2-11. Me Me H H — H T6 2-12. Me MeH H — Na T6 2-13. Me Me H H — H T7 2-14. Me Me H H — Na T7 2-15. Me MeMe H — H T1 2-16. Me Me Me H — Na T1 2-17. Me Me Me H — H T2 2-18. Me MeMe H — Na T2 2-19. Me Me Me H — H T5 2-20. Me Me Me H — Na T5 2-21. MeMe Me H — H T6 2-22. Me Me Me H — Na T6 2-23. Me Me Me H — H T7 2-24. MeMe Me H — Na T7 2-25. Me Me H H 5-Me H T1 2-26. Me Me H H 5-Me Na T12-27. Me Me H H 5-Me H T2 2-28. Me Me H H 5-Me Na T2 2-29. Me Me H H 5-FH T1 2-30. Me Me H H 5-F Na T1 2-31. Me Me H H 5-F H T2 2-32. Me Me H H5-F Na T2 2-33. Me Me H H 5-Cl H T1 2-34. Me Me H H 5-Cl Na T1 2-35. MeMe H H 5-OMe H T1 2-36. Me Me H H 5-OMe Na T1 2-37. Me Me H H 5-NO₂ H T12-38. Me Me H H 5-NO₂ Na T1 2-39. Me Me H H 6-Me H T1 2-40. Me Me H H6-Me Na T1 2-41. Me Me H H 6-Cl H T1 2-42. Me Me H H 6-Cl Na T1 2-43. MeMe Me H 5-Me H T1 2-44. Me Me Me H 5-Me Na T1 2-45. Me Me Me H 5-Cl H T12-46. Me Me Me H 5-Cl Na T1 2-47. Me Me Me H 5-OMe H T1 2-48. Me Me Me H5-OMe Na T1 2-49. Me Me Me H 5-NO₂ H T1 2-50. Me Me Me H 5-NO₂ Na T12-51. Me Me Me H 6-Me H T1 2-52. Me Me Me H 6-Me Na T1 2-53. Me Me Me H6-Cl H T1 2-54. Me Me Me H 6-Cl Na T1

TABLE 3 Compounds of the formula (VIII) (VIII)

Ex. No. R¹ Q R⁴ R⁵ Het m.p. 3-1. Me O — H T1 3-2. Me O — Me T1 161-1633-3. Me O — H T2 212-214 3-4. Me O — H T3 218-220 3-5. Me O — H T4 3-6.Me O — H T5 3-7. Me O — H T6 3-8. Me O — H T7 211-213 3-9. Me O — H T83-10. Me O — H T9 3-11. Me O — H T10 3-12. Me O — H T11 3-13. Me O — HT12 3-14. Me O — H T13 3-15. Me O — H T14 3-16. Me O — H T15 3-17. Me O— H T16 3-18. Me O — H T17 3-19. Me O — H T18 3-20. Me O — H T19 3-21.Me O — H T20 3-22. Et O — H T1 223-225 3-23. Et O — H T2 194-196 3-24.Et O — H T6 3-25. Et O — H T7 3-26. Me NMe — H T1 3-27. Me NMe — H T23-28. Me NMe — H T6 3-29. Me NMe — H T7

B. Formulation Examples

-   a) A dust is obtained by mixing 10 parts by weight of a compound of    the formula (I) and 90 parts by weight of talc as inert substance    and comminuting the mixture in a hammer mill.-   b) A wettable powder which is readily dispersible in water is    obtained by mixing 25 parts by weight of a compound of the formula:    (I), 64 parts by weight of kaolin-containing quartz as inert    substance, 10 parts by weight of potassium lignosulfonate and 1 part    by weight of sodium oleoylmethyltaurinate as Wetter and dispersant    and grinding the mixture in a pinned-disk mill.-   c) A dispersion concentrate which is readily dispersible in water is    obtained by mixing 20 parts by weight of a compound of the    formula (I) with 6 parts by weight of alkylphenol polyglycol ether    (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether    (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling    range for example approx. 255 to above 277° C.) and grinding the    mixture in a ball mill to a fineness of below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I), 75 parts by weight of    cyolohexanone as the solvent and 10 parts by weight of ethoxylated    nonylphenol as the emulsifier.-   e) Water-dispersible granules are obtained by mixing    -   75 parts by weight of a compound of the formula (I),    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium lauryl sulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin    -   grinding the mixture on a pinned-disk mill and granulating the        powder in a fluidized bed by spraying on water as the        granulation liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting, on a colloid mill,    -   25 parts by weight of a compound of the formula (I),    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate    -   2 parts by weight of sodium oleoylmethyltaurinate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water,    -   subsequently grinding the mixture in a bead mill and atomizing        and drying the resulting suspension in a spray tower by means of        a single-substance nozzle.

C. Biological Examples

1. Pre-Emergence Effect on Weeds

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weedplants were placed in sandy loam soil in cardboard pots and covered withsoil. The compounds according to the invention which were formulated inthe form of wettable powders or emulsion concentrates were then appliedto the surface of the soil cover in the form of aqueous suspensions oremulsions at an application rate of 600 to 800 l of water/ha(converted), in various dosages.

After the treatment, the pots were placed in a greenhouse and kept undergood growth conditions for the weeds. After the test plants had emerged,the damage to the plants or the negative effect on the emergence wasscored visually after a test period of 3 to 4 weeks by comparison withuntreated controls. As shown by the test results, compounds according tothe invention have good herbicidal pre-emergence activity against abroad spectrum of weed grasses and broad-leafed weeds. For example, thecompounds of Example Nos. 1-9, 1-11, 1-15, 1-16, 1-17, 1-23, 1-25, 1-26,1-41, 145, 1-47, 1-55, 1-57, 1-105, 1-129, 1-131, 1-135, 1-153, 1-154,1-155, 1-159, 1-177, 1-179, 1-189, 1-241, 1-243, 1-247, 1-265, 1-267,1-271, 1-353, 1-355, 1-359, 1-381, 1-383, 1-387, 1-401, 1-417, 1-425,1-426, 1-433, 1-435, 1-439, 1-453, 1-455, 1-459 and other compounds ofTables 1 and 2 have very good herbicidal activity against harmful plantssuch as Sinapis alba, Chrysanthemum segetum, Avena sativa, Stellariamedia, Echinochloa crus-galli, Lolium multiflorum, Setaria spp.,Abutilon theophrasti, Amaranthus retroflexus and Panicum miliaceum,pre-emergence at an application rate of 0.3 kg and less of activesubstance per hectar.

2. Post-Emergence Effect on Weeds

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weedswere placed in sandy loam soil in plastic pots, covered with soil andgrown in a greenhouse under good growth conditions. Three weeks aftersowing, the test plants were treated at the three-leaf stage. Thecompounds according to the invention which were formulated as wettablepowders or emulsion concentrates were sprayed, at various dosages, ontothe green parts of the plants at an application rate of 600 to 800 l ofwater/ha (converted). After the test plants had remained in thegreenhouse for about 3 to 4 weeks under ideal growth conditions, theeffect of the preparations was scored visually by comparison withuntreated controls. The agents according to the invention also have goodherbicidal activity post-emergence against a broad spectrum ofeconomically important Weed grasses and broad-loafed weeds. For example,the compounds of Example Nos. 1-9, 1-11, 1-15, 1-16, 1-17, 1-23, 1-25,1-26, 141, 145, 147, 1-55, 1-57, 1-105, 1-129, 1-131, 1-135, 1-153,1-154, 1-155, 1-159, 1-177, 1-179, 1-189, 1-241, 1-243, 1-247, 1-265,1-267, 1-271, 1-353, 1-355, 1-359, 1-381, 1-383, 1-387, 1-401, 1-417,1-425, 1-426, 1-433, 1-435, 1-439, 1-453, 1-455, 1-459 and othercompounds of Tables 1 and 2 have very good herbicidal activity againstharmful plants such as Sinapis alba, Echinochloa crus-galli, Loliummultiflorum, Chrysanthemum segetum, Setaria spp., Abutilon theophrasti,Amaranthus retroflexus, Panicum miliaceum and Avena sativapost-emergence at an application rate of 0.3 kg and less of activesubstance per hectare.

3. Tolerance by Crop Plants

In further greenhouse experiments, seeds of a substantial number of cropplants and weeds were placed in sandy loam soil and covered with soil.Some of the pots were treated immediately as described under Section 1,and the remaining pots were placed in the greenhouse until the plantshad developed two to three true leaves and then sprayed with variousdosages of the substances of the formula (I) according to the invention,as described under Section 2. Visual scoring four to five weeks afterthe application and after the plants had been in the greenhouse revealedthat compounds according to the invention left dicotyledonous crops suchas soya, cotton, oilseed rape, sugar beet or potatoes unharmed even whenhigh dosages of active ingredient were used by the pre- andpost-emergence method. Moreover, some substances also spared Gramineaecrops such as barley, wheat, rye, sorghum species, corn or rice. Some ofthe compounds of the formula (I) have high selectivity, and they aretherefore suitable for controlling undesirable vegetation inagricultural crops.

1-17. (canceled)
 18. A compound of the formula (I) or a salt thereof

in which R¹ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, whereeach of the three last-mentioned radicals is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, unsubstituted and substituted phenyl, unsubstituted andsubstituted heterocyclyl, unsubstituted and substituted(C₃-C₆)cycloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,[(C₁-C₄)alkoxy]carbonyl and [(C₁-C₄)haloalkoxy]carbonyl, or isunsubstituted or substituted (C₃-C₆)cycloalkyl, substituted orunsubstituted (C₃-C₆)cycloalkenyl, unsubstituted or substituted phenyl,unsubstituted or substituted heterocyclyl having 3 to 6 ring atoms,where substituted phenyl, substituted heterocyclyl, substitutedcycloalkyl or substituted cycloalkenyl carry, as substituents, one ormore radicals selected from the group consisting of halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkyl,di[(C₁-C₄)alkoxy](C₁-C₄)alkyl, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, NR⁸R⁹, [(C₁-C₄)alkoxy]carbonyl,[(C₁-C₄)haloalkoxy]carbonyl, [(C₁-C₄)alkyl]carbonyl, OH, phenyl, CN andNO₂ and R² is a group of the formula R⁰-Q⁰-, in which R⁰ is a hydrogenatom, (C₁-C₁₂)alkyl, (C₂-C₁₂)alkenyl or (C₂-C₁₂)alkynyl, where each thethree last-mentioned radicals is unsubstituted or substituted by one ormore radicals selected from the group consisting of halogen,(C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl,(C₁-C₆)alkylsulfonyl, (C₁-C₆)haloalkylsulfonyl, [(C₁-C₆)alkoxy]carbonyl,[(C₁-C₆)haloalkoxy]carbonyl, CONR⁶R⁷, SO₂NR⁶R⁷, CN, OH, SH,(C₃-C₆)cycloalkyl, NR⁸R⁹, unsubstituted or substituted phenyl, andunsubstituted or substituted heterocyclyl, or is (C₃-C₆)cycloalkyl,(C₃-C₆)cycloalkenyl, phenyl or heterocyclyl, where the fourlast-mentioned radicals may be unsubstituted or substituted, and inwhich Q⁰ is a direct bond or a divalent group of the formula —O— or—N(R^(#))— where R^(#) is a hydrogen atom, CHO, SO₂CH₃, an acyl radicalor (C₁-C₁₂)alkyl, (C₂-C₁₂)alkenyl or (C₂-C₁₂)alkynyl, where each of the3 last-mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio, CN. OH,(C₃-C₆)cycloalkyl, unsubstituted or substituted phenyl, andunsubstituted or substituted heterocyclyl, or is unsubstituted orsubstituted (C₃-C₆)cycloalkyl, unsubstituted or substituted(C₃-C₆)cycloalkenyl or unsubstituted or substituted phenyl, and R⁰ andR^(#) together with the nitrogen atom of the NR^(#)R⁰ group may form aheterocyclyl radical, having 3 to 6 ring atoms, which is unsubstitutedor substituted by one or more radicals selected from the groupconsisting of halogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy,[(C₁-C₆)alkoxy]carbonyl, (C₁-C₆)haloalkyl and oxo, R³ is a hydrogenatom, (C₁-C₁₂)alkyl; (C₂-C₁₂)alkenyl or (C₂-C₁₂)alkynyl, where each ofthe 3 last-mentioned radicals is unsubstituted or substituted by one ormore radicals selected from the group consisting of halogen,(C₁-C₆)alkoxy, (C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio,(C₁-C₆)haloalkylthio, (C₁-C₆)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl,(C₁-C₆)alkylsulfonyl, (C₁-C₆)haloalkylsulfonyl, [(C₁-C₆)alkoxy]carbonyl,[(C₁-C₆)haloalkoxy]carbonyl, CONR⁶R⁷, SO₂NR⁶R⁷, CN, OH,(C₃-C₆)cycloalkyl, NR⁸R⁹, unsubstituted or substituted phenyl, andunsubstituted or substituted heterocyclyl, or is unsubstituted orsubstituted (C₃-C₆)cycloalkyl, unsubstituted or substituted(C₃-C₆)cycloalkenyl, unsubstituted or substituted heterocyclyl, orunsubstituted or substituted phenyl, or R² and R³ together with thenitrogen atom of the NR²R³ group (N¹) form a heterocyclyl radical,having 3 to 6 carbon ring atoms, which is unsubstituted or substitutedand which one of the carbon atoms is optionally replaced by oneheteroatom selected from the group consisting of N, O, and S, by one ormore radicals selected from the group consisting of halogen,(C₁-C₆)alkyl, (C₁-C₆)alkoxy, [(C₁-C₆)alkoxy]carbonyl, (C₁-C₆)haloalkyland oxo, where the oxo radical is not adjacent to the nitrogen atom(N¹), and R⁴ independently of one another are halogen NH₂, NO₂, NHOH,NO, NH—NH₂, N₃, CN, (C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₆)alkenyl,(C₂-C₆)alkynyl, (C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, where each of the6 last-mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio,(C₁-C₆)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, [(C₁-C₆)alkoxy]carbonyl,[(C₁-C₆)haloalkoxy]carbonyl, CONR⁶R⁷, SO₂NR⁶R⁷, CN, OH,(C₃-C₆)cycloalkyl, NR⁸R⁹, unsubstituted or substituted phenyl orunsubstituted or substituted heterocyclyl, or is unsubstituted orsubstituted (C₃-C₆)cycloalkyl, unsubstituted or substituted(C₃-C₆)cycloalkenyl, unsubstituted or substituted heterocyclyl,unsubstituted or substituted phenyl, [(C₁-C₄)alkyl]carbonyl or[(C₁-C₄)alkoxy]carbonyl, where each of the two last-mentioned radicalsis unsubstituted or substituted in the alkyl moiety by one or morehalogen atoms, or is a radical of the formula C(O)—NR′—R″, C(S)—NR′—R″,CR′═N-Q¹-R″, S(O)_(m)-Q¹-R″″, P(O)_(n)(-Q¹-R″″Q²-R″), NR′-Q¹-R″ orNR′″—N═CR′—R″, where R′, R″ and R′″ independently of one another are ahydrogen atom, an acyl radical or an unsubstituted or substituted(C₁-C₁₀)hydrocarbon radical, R″″ is a carbon-containing acyl radical oran unsubstituted or substituted (C₁-C₁₀)hydrocarbon radical, and Q¹ andQ² independently of one another are a direct bond or a divalent group ofthe formula —O— or —N(R⁺)—, where R⁺ is a hydrogen atom, an arylradical, or an unsubstituted or substituted (C₁-C₁₀)hydrocarbon radical,and m=0, 1, 2 or 3, and n=0, 1 or 2, and R′ together with R″, R⁺together with R′, R⁺ together with R″ or R⁺ together with R″″ may ineach case form a heterocyclyl radical having 3 to 6 carbon ring atomswhich is unsubstituted by one or more radicals selected from the groupconsisting of halogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy,[(C₁-C₆)alkoxy]carbonyl, (C₁-C₆)haloalkyl and oxo, I is 0, 1 or 2; R⁵ isH or (C₁-C₄)alkyl which is unsubstituted or substituted, R⁶ and R⁷independently of one another are H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl,(C₃-C₆)alkynyl, unsubstituted or substituted phenyl or unsubstituted orsubstituted heterocyclyl or R⁶ and R⁷ together with the nitrogen atom ofthe NR⁶R⁷ group may form a heterocyclyl radical having 5 or 6 carbonatoms which may optionally be replaced by one heteroatom selected fromthe group consisting of N, O and S and which is unsubstituted or mono-or polysubstituted by radicals selected from the group consisting of(C₁-C₄)alkyl and oxo, and R⁸ and R⁹ independently of one another are(C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, (C₁-C₄)alkoxycarbonyl or(C₁-C₄)alkylsulfonyl or together with the nitrogen atom, of the NR⁸R⁹group may form a heterocyclyl radical having 5 or 6 carbon ring atomswhich may be optionally replaced by one additional heteroatom selectedfrom the group consisting of N, O and S and which is unsubstituted ormono- or polysubstituted by radicals selected from the group consistingof (C₁-C₄)alkyl and oxo, Q is O, S or NR*, R* is (C₁-C₄)alkyl,(C₃-C₄)alkenyl or (C₃-C₄)alkynyl, where each of the three last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₄)alkoxy and(C₁-C₄)alkylthio, and R* and R¹ together with the nitrogen atom of theNR*R¹ group may form a heterocyclyl radical which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₆))alkyl, (C₁-C₆)alkoxy, [(C₁-C₆)alkoxy]carbonyl,(C₁-C₆)haloalkyl and oxo, W is an oxygen atom or a sulfur atom, V and Zis CH or N, wherein at least one of V and Z is CH and the other is CH orN. X, Y independently of one another are H, halogen, (C₁-C₄)alkyl,(C₁-C₄)alkoxy, (C₁-C₄)alkylthio, where each of the three last-mentionedradicals is unsubstituted or substituted by one or more radicals fromthe group consisting of halogen, (C₁-C₄)alkoxy and (C₁-C₄)alkylthio, aremono- or di[(C₁-C₄)alkyl]amino, (C₃-C₅)alkenyl, (C₃-C₅)alkenyloxy,(C₃-C₅)alkynyl or (C₃-C₅)alkynyloxy, and where the radicals R¹, R², R³,and R⁴, including substituents, have up to 20 carbon atoms, and wherein,if not otherwise specified: heterocyclyl is a saturated or unsaturatedring having 3 to 7 ring atom or a heteroaromatic ring having 5 or 6 ringatoms, and wherein one of the ring atoms is a heteroatom selected fromthe group consisting of N, O, or S and the remaining ring atoms arecarbon atoms or is a radical selected from the group consisting ofpyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, oxazolyl,pyrazolyl, and imidazolyl, pyrrolidyl, piperidyl, piperazinyl,dioxolanyl, or morpholinyl; substituents for the (C₃-C₆)cycloalkyl,(C₃-C₆) cycloalkenyl, phenyl, or heterocyclic rings or the(C₁-C₁₀)hydrocarbon radical, unless otherwise specified are 1, 2, or 3radicals selected from the group consisting of halogen, alkoxy,haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido,alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- anddialkylaminocarbonyl, acylamino, NR⁸R⁹, mono-, and dialkylamino, andalkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,alkyl and haloalkyl alkenyl, alkynyl, alkenyloxy, alkynyloxy, and phenylwhich is optionally substituted by one or more radicals selected fromthe group consisting of halogen, (C₁-C₄) alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, [(C₁-C₄)alkoxy]carbonyl,[(C₁-C₄)alkyl]carbonyl, NR⁸R⁹, phenyl, CN and NO₂.
 19. The compound ofclaim 18, wherein at least one of V and Z is CH and the other is N. 20.The compound of claim 19, wherein V is N and Z is CH.
 21. The compoundof the formula (I) or salt thereof according to claim 18, in which R¹ is(C₁-C₆)alkyl which is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen and(C₁-C₄)alkoxy, or is 3-oxetanyl, (C₃-C₄)alkenyl or (C₃-C₄)alkynyl, R² isH, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, where each of the threelast-mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, (C₁-C₄)alkoxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfonyl, [(C₁-C₄)alkoxy]carbonyl,(C₃-C₆)cycloalkyl, CN and OH, or is (C₃-C₆)cycloalkyl which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,[(C₁-C₄)alkoxy]carbonyl, CN and OH, or is (C₃-C₆)cycloalkenyl,(C₁-C₄)alkoxy, (C₁-C₄)alkenyloxy, (C₁-C₄)alkylamino ordi[(C₁-C₄)alkyl]amino and R³ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl,(C₃-C₆)alkynyl, where each of the three last-mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfonyl, [(C₁-C₄)alkoxy]carbonyl; (C₃-C₆)cycloalkyl, CN andOH, or is (C₃-C₆)cycloalkyl which is unsubstituted or -substituted byone or more radicals selected from the group consisting of halogen,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, [(C₁-C₄)alkoxy]carbonyl, CN and OH, or is(C₃-C₆)cycloalkenyl or R² and R³ together with the nitrogen atom (N¹)may form a heterocyclyl of 3 to 6 carbon ring and which is unsubstitutedor substituted by one or more radicals selected from the groupconsisting of halogen, (C₁-C₆)alkyl, (C₁-C₆)alkoxy,[(C₁-C₃)alkoxy]carbonyl and oxo, where the oxo radical is not adjacentto the nitrogen atom (N¹), and R⁴ are (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy or halogen, NH₂, NO₂, NHOH, NO, NH—NH₂ or NH₃ I is 0 or 1,R⁵ is H or C₁-C₄ alkyl, Q is O or NR*, R* is H or (C₁-C₄)alkyl,(C₃-C₄)alkenyl, or (C₃-C₄)alkynyl X and Y independently of one anotherare (C₁-C₄)alkyl, (C₁-C₄)alkoxy, where each of the two last-mentionedradicals is unsubstituted or substituted by one or more halogen atoms,or are (C₁-C₄)alkylthio, halogen or mono- or di[(C₁-C₂)alkyl]amino, andW is an oxygen atom or a sulfur atom.
 22. A compound or salt thereofaccording to claim 18 wherein R¹ is (C₁-C₆)alkyl which is unsubstitutedor substituted by one or more radicals selected from the groupconsisting of halogen and (C₁-C₄)alkoxy, or is 3-oxetanyl,(C₃-C₄)alkenyl or (C₃-C₄)alkynyl, R² is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl,(C₃-C₆)alkynyl, where each of the three last-mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfonyl, [(C₁-C₄)alkoxy]carbonyl, (C₃-C₆)cycloalkyl, CN andOH, or is (C₃-C₆)cycloalkyl which is unsubstituted or substituted by oneor more radicals selected from the group consisting of halogen,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, [(C₁-C₄)alkoxy]carbonyl, CN and OH, or is(C₃-C₆)cydoalkenyl, (C₁-C₄)alkoxy, (C₁-C₄)alkenyloxy, (C₁-C₄)alkylaminoor di[(C₁-C₄)alkyl]amino and R³ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl,(C₃-C₆)alkynyl, where each of the three last-mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfonyl, [(C₁-C₄)alkoxy] carbonyl, (C₃-C₆)cycloalkyl, CNand OH, or is (C₃-C₆)cycloalkyl which is unsubstituted or substituted byone or more radicals selected from the group consisting of halogen,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, [(C₁-C₄)alkoxy]carbonyl, CN and OH, or is(C₃-C₆)cycloalkenyl or R² and R³ together with the nitrogen atom (N¹)may form heterocyclic ring of the formulae:

unsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₆)alkyl, (C₁-C₃)alkoxy,[(C₁-C₃)alkoxy]carbonyl and oxo, and R⁴ are (C₁-C₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy or halogen, I is 0 or 1, R⁵ is H ormethyl, Q is O, X and Y independently of one another are (C₁-C₄)alkyl,(C₁-C₄)alkoxy, where each of the two last-mentioned radicals isunsubstituted or substituted by one or more halogen atoms, or are(C₁-C₄)alkylthio, halogen or mono- or di[(C₁-C₂)alkyl]amino, and W is anoxygen atom.
 23. A compound of the formula (I) or a salt thereof asclaimed in claim 18 in which R¹ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl or(C₃-C₆)alkynyl, where each of the three last-mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, phenyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₃-C₆)cycloalkyl or heterocyclyl having 3 to 6 ring atoms and[(C₁-C₄)alkoxy]carbonyl, or is (C₃-C₆)cycloalkyl, heterocyclyl having 3to 6 ring atoms, where each of the two last-mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl and (C₁-C₄)alkoxy, R² is agroup of the formula R⁰-Q⁰- in which R⁰ is a hydrogen atom,(C₁-C₈)alkyl, (C₃-C₈)alkenyl or (C₃-C₈)alkynyl, where each of the threelast-mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, [(C₁-C₆)alkoxy]carbonyl, CONR⁶R⁷, SO₂NR⁶R⁷,CN, OH, (C₃-C₆)cycloalkyl, NR⁸R⁹ and phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, NR⁸R⁹, [(C₁-C₄)alkoxy]carbonyl, [(C₁-C₄)alkyl]carbonyl, phenyl [(C₁-C₄)alkyl]carbonyl, CN and NO₂, or isheterocyclyl having 3 to 6 ring atoms which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, NR⁸R⁹, [(C₁-C₄)alkoxy]carbonyl,[(C₁-C₄)alkyl]carbonyl, phenyl, CN and NO₂, or is (C₃-C₆)cycloalkylwhich is unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, (C₁-C_(C) ₄)alkyl,(C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy,[(C₁-C₄)alkoxy]carbonyl, CN, OH and phenyl, or is (C₃-C₆)cycloalkenylwhich is unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy and [(C₁-C₄)alkoxy]carbonyl, or is phenyl which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)alkylsulfonyl, NR⁸R⁹,[(C₁-C₄)alkoxy]carbonyl, [(C₁-C₄)alkyl]carbonyl, phenyl, CN and NO₂, andQ⁰ is a direct bond or a divalent group of the formula —O or —NR^(#), inwhich R^(#) is a hydrogen atom, CHO, CO(CH₃), SO₂(CH₃) or unsubstitutedor substituted (C₁-C₄)alkyl, R³ is a hydrogen atom, (C₁-C₈)alkyl,(C₃-C₈)alkenyl or (C₃-C₈)akynyl, where each of the three last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)haloalkylthio,(C₁-C₄)alkylsulfinyl, (C₁-C₄)haloalkylsulfinyl, (C₁-C₄)alkylsulfonyl,(C₁-C₄)haloalkylsulfonyl, [(C₁-C₆)alkoxy]carbonyl, CONR⁶R⁷, SO₂NR⁶R⁷,CN, OH, (C₃-C₆)cycloalkyl, NR⁸R⁹ and phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsufonyl, NR⁸R⁹, [(C₁-C₄)alkoxy]carbonyl,[(C₁-C₄)alkyl]carbonyl, phenyl, [(C₁-C₄)alkyl]carbonyl, CN and NO₂, oris heterocyclyl having 3 to 6 ring atoms which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, NR⁸R⁹, [(C₁-C₄)alkoxy]carbonyl,[(C₁-C₄)alkyl]carbonyl, phenyl, CN and NO₂, or is (C₃-C₆)cycloalkylwhich is unsubstituted or substituted by one or more radicals selectedfrom the group consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy, (C₁-C₄)haloalkoxy, [(C₁-C₄)alkoxy]carbonyl, CN, OH andphenyl, or is (C₃-C₆)cycloalkenyl which is unsubstituted or substitutedby one or more radicals selected from the group consisting of halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, and[(C₁-C₄)alkoxy]carbonyl, or is phenyl which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy,(C₁-C₄)haloalkoxy, (C₁-C₄)alkylthio, (C₁-C₄)alkylsulfinyl,(C₁-C₄)alkylsulfonyl, NR⁸R⁹, [(C₁-C₄)alkoxy]carbonyl,[(C₁-C₄)alkyl]carbonyl, phenyl, CN and NO₂, and R⁴ are halogen, CN,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, (C₂-C₆)alkenyl, (C₂-C₆)alkynyl(C₃-C₆)alkenyloxy, (C₃-C₆)alkynyloxy, where each of the 6 last-mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₆)alkoxy,(C₁-C₆)haloalkoxy, (C₁-C₆)alkylthio, (C₁-C₆)haloalkylthio,(C₁-C₆)alkylsulfinyl, (C₁-C₆)haloalkylsulfinyl, (C₁-C₆)alkylsulfonyl,(C₁-C₆)haloalkylsulfonyl, [(C₁-C₆)alkoxy]carbonyl,[(C₁-C₆)haloalkoxy]carbonyl, CONR⁶R⁷, SO₂NR⁶R⁷, CN, OH,(C₃-C₆)cycloalkyl, NR⁸R⁹, unsubstituted or substituted phenyl,unsubstituted or substituted heterocyclyl or are unsubstituted orsubstituted (C₃-C₆)cycloalkyl, unsubstituted or substituted(C₃-C₆)cycloalkenyl, unsubstituted or substituted heterocyclyl having 3to 6 ring atoms, unsubstituted or substituted phenyl or[(C₁-C₄)alkyl]carbonyl or [(C₁-C₄)alkoxy]carbonyl, where each of the twolast-mentioned radicals is unsubstituted or substituted in the alkylmoiety by one or more halogen atoms or are radicals of the formulaC(O)—NR′—R″, C(S)—NR′—R″, CR′═N-Q¹-R″, NR′-Q¹-R″ or NR′″-N═CR′—R″ whereR′, R″ and R′″ independently of one another are a hydrogen atom, an acylradical or an unsubstituted or substituted (C₁-C₁₀)hydrocarbon radical,and Q¹ and Q² independently of one another are a direct bond or adivalent group of the formula —O— or —N(R⁺)—, where R⁺ is a hydrogenatom, an acyl radical or an unsubstituted or substituted (C₁-C₄)alkylradical and R′ together with R″ or R⁺ together with R′ or R⁺ togetherwith R″ may in each case form a heterocyclyl radical having 3 to 6 ringatoms which is unsubstituted or substituted, 1 is 0 or 1, R⁶ and R⁷independently of one another are H, (C₁-C₄)alkyl, (C₃-C₄)alkenyl,(C₃-C₄)alkynyl or phenyl which is unsubstituted or substituted by one ormore radicals selected from the group consisting of halogen,(C₁-C₄)alkyl, (C₁-C₄)haloalkyl, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfonyl, [(C₁-C₄)alkoxy]carbonyl, CN and NO₂, or R⁶ and R⁷together with the nitrogen atom of the NR⁶R⁷ group may form aheterocyclyl radical having 5 to 6 ring members which may be replaced byone heteroatom selected from the group consisting of N, O, and S andwhich is unsubstituted or mono- or polysubstituted by radicals selectedfrom the group consisting of (C₁-C₄)alkyl and oxo, R⁸ and R⁹ are(C₁-C₄)alkylcarbonyl, (C₁-C₄)haloalkylcarbonyl, (C₁-C₄)alkoxycarbonyl or(C₁-C₄)alkylsulfonyl, or together with the nitrogen atom of the NR⁸R⁹group may form a heterocyclyl radical having 5 to 6 ring members whichmay contain one heteroatom selected from the group consisting of N, O,and S and which is unsubstituted or mono- or polysubstituted by radicalsselected from the group consisting of (C₁-C₄)alkyl and oxo.
 24. Acompound of the formula (I) or a salt thereof as claimed in claim 18 inwhich R¹ is (C₁-C₆)alkyl which is unsubstituted or substituted by one ormore radicals selected from the group consisting of halogen and(C₁-C₄)alkoxy, or is 3-oxetanyl, (C₃-C₄)alkenyl or (C₃-C₄)alkynyl, R² isH, (C₁-C₆)alkyl, (C₃-C₆)alkenyl, (C₃-C₆)alkynyl, where each of the threelast-mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, (C₁-C₄)alkoxy,(C₁-C₄)alkylthio, (C₁-C₄)alkylsulfonyl, [(C₁-C₄)alkoxy]carbonyl,(C₃-C₆)cycloalkyl, CN and OH, or is (C₃-C₆)cycloalkyl which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkyl, (C₁-C₄)alkoxy,[(C₁-C₄)alkoxy]carbonyl, CN and OH, or is (C₃-C₆)cycloalkenyl,(C₁-C₄)alkoxy, (C₁-C₄)alkenyloxy, (C₁-C₄)alkylamino ordi[(C₁-C₄)alkyl]amino and R³ is H, (C₁-C₆)alkyl, (C₃-C₆)alkenyl,(C₃-C₆)alkynyl, where each of the three last-mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)alkoxy, (C₁-C₄)alkylthio,(C₁-C₄)alkylsulfonyl, [(C₁-C₄)alkoxy]carbonyl, (C₃-C₆)cycloalkyl, CN andOH, or is (C₃-C₆)cycloalkyl which is unsubstituted or substituted by oneor more radicals selected from the group consisting of halogen,(C₁-C₄)alkyl, (C₁-C₄)alkoxy, [(C₁-C₄)alkoxy]carbonyl, CN and OH, or is(C₃-C₆)cycloalkenyl or R² and R³ together with the nitrogen atom (N¹)may form a heterocyclyl of 3 to 6 carbon ring atoms which contain oneheteroatom selected from the group consisting of N, O, and S and whichis unsubstituted or substituted by one or more radicals selected fromthe group consisting of halogen, (C₁-C₆)alkyl, (C₁-C₃)alkoxy,[(C₁-C₃)alkoxy]carbonyl and oxo, R⁴ are (C₁-C₄)alkyl, (C₁-C₄)haloalkyl,(C₁-C₄)alkoxy or halogen, I is 0 or 1, R⁵ is H or methyl, Q is O or NR*,R* is H or (C₁-C₄)alkyl, X and Y independently of one another are(C₁-C₄)alkyl, (C₁-C₄)alkoxy, where each of the two last-mentionedradicals is unsubstituted or substituted by one or more halogen atoms,or are (C₁-C₄)alkylthio, halogen or mono- or di[(C₁-C₂)alkyl]amino, andW is an oxygen atom.
 25. A compound of the formula (I) or a salt thereofas claimed in claim 18 in which R¹ is (C₁-C₃)alkyl, allyl, or propargyl,R² is H, (C₁-C₄)alkyl, (C₃-C₅)alkenyl, (C₃-C₅)alkynyl, (C₃-C₆)cycloalkylor (C₃-C₆)cycloalkenyl, or R³ is H, (C₁-C₄)alkyl, (C₃-C₅)alkenyl,(C₃-C₅)alkynyl, (C₃-C₆)cycloalkyl or (C₃-C₆)cycloalkenyl, or R² and R³together with the nitrogen atom (N¹) may form a heterocyclyl of 3 to 6ring carbon atoms in which one of the carbon atoms is optionallyreplaced by one heteroatom selected from the group consisting of N, O,and S and which is unsubstituted or substituted by one or more(C₁-C₆)alkyl radicals, R⁴ are (C₁-C₃)alkyl or halogen, I is 0 or 1, Q isO or NR*, R* is (C₁-C₃)alkyl, X is (C₁-C₂)alkyl, (C₁-C₂)alkoxy,(C₁-C₂)alkylthio, (C₁-C₂haloalkyl or (C₁-C₂)haloalkoxy, Y is(C₁-C₂)alkyl, (C₁-C₂)alkoxy, halogen, NHCH₃ or N(CH₃)₂.
 26. A processfor preparing compounds of the formula (I) or salts thereof as definedin claim 18 which comprises a) reacting a compound of the formula (II)

with a heterocyclic carbamate of the formula (III),

in which R** is a substituted or unsubstituted C₁-C₂₀-hydrocarbonradical, or b) reacting a sulfonylcarbamate of the formula (IV),

in which R*** is a substituted or unsubstituted C₁-C₂₀-hydrocarbonradical with an amino heterocycle of the formula (V)

or c) reacting a sulfonyl isocyanate of the formula (VI)

with an amino heterocycle of the formula (V) or d) reacting asulfonamide of the formula (II) with a (thio)isocyanate of the formula(VII)

in the presence of a base or d) reacting an amino heterocycle of theformula (V) initially under base catalysis with a carbonic ester andreacting the resulting intermediate in a one-pot reaction with asulfonamide of the formula (II) (see variant a), or f) reacting aphenylsulfonyl urea of the formula (VIII)

by the reduction of the nitro group and, if appropriate, furtherconversion of the hydroxylamine or amine function that is released togive the sulfonyl urea of the formula (I), wherein the formulae (II) to(VIII) the radicals, groups and indices R¹, R⁵, Q, V, W, X, Y, Z, and 1are as defined in formula (I) of the claim
 18. 27. A herbicidalplant-growth regulating composition comprising a) one or more compoundsof the formula I or a salt thereof as claimed in claim 18, and b)formulation auxiliaries which are customary in crop protection.
 28. Amethod for controlling harmful plants or for regulating the growth ofplants, which comprises applying an effective amount of one or morecompounds of the formula (I) or a salt thereof as claimed in claim 18 tothe harmful plants or plants, to their plant seeds or to the area onwhich they grow.
 29. The compound of claim 18, wherein: R¹ is H, methyl,ethyl, i-propyl, allyl, or 3-oxetanyl; R² is a group of the formulaR⁰-Q⁰-, in which R⁰ is hydrogen, methyl, ethyl, i-propyl, cyclopropyl,CH₂-i-propyl, CH₂CH₂F, CH₂CH₂CF₃, CH₂CH₂CH₂CF₃, CH(CH₃)CH₂C(O)OCH₃,CH(CH₃)CH₂C(O)NR⁶R⁷, CH(CH₃)CH₂CH₃, allyl, propargyl, methoxy, CH₂Ph,CH₂OCH₃, CH₂C(O)CH₃, CH₂C(O)OCH₃ and Q⁰ is a direct bond or —N(R^(#));R³ is H, methyl, ethyl, i-propyl, CH₂-1-propyl; or R² and R³ togetherwith the nitrogen atom of the NR²R³ group (N¹) forms a heterocycleselected from the group consisting of:

R^(#) is methyl, CHO, CO(CH₃) or SO₂(CH₃); R⁴ is methyl, fluoro, chloro,methoxy, or NO₂; I is 0 or 1; R⁵ is H or methyl; R⁶ is H; R⁷ is H; R⁸and R⁹ is independently of one another are H, methyl, Q is oxygen orNR*; R* is H or methyl; W is oxygen; V is N; X, Y independently of oneanother are chloro, methyl, CF₃, methoxy, ethoxy, —SMe or —OCHF₂; and Zis CH.
 30. The compound of claim 18, wherein: R¹ is H, methyl, ethyl,i-propyl, allyl, or 3-oxetanyl; R² is a group of the formula R⁰-Q⁰-, inwhich R⁰ is hydrogen, methyl, ethyl, i-propyl, cyclopropyl,CH₂-i-propyl, CH₂CH₂F, CH₂CH₂CF₃, CH₂CH₂CH₂CF₃, CH(CH₃)CH₂C(O)OCH₃,CH(CH₃)CH₂C(O)NR⁶R⁷, CH(CH₃)CH₂CH₃, allyl, propargyl, methoxy, CH₂Ph,CH₂OCH₃, CH₂C(O)CH₃, CH₂C(O)OCH₃ and Q⁰ is a direct bond or —N(R^(#));R³ is H, methyl, ethyl, i-propyl, CH₂-1-propyl; or R² and R³ togetherwith the nitrogen atom of the NR²R³ group (N¹) forms a heterocycleselected from the group consisting of:

R^(#) is methyl, CHO, CO(CH₃) or SO₂(CH₃); R⁴ is methyl, fluoro, chloro,methoxy, or NO₂; I is 0 or 1; R⁵ is H or methyl; Q is oxygen; W isoxygen; V is N; X, Y independently of one another are chloro, methyl,CF₃, methoxy, ethoxy, —SMe or —OCHF₂; and Z is CH.
 31. The compound ofclaim 18, wherein: R¹ is H or methyl; R² is a group of the formulaR⁰-Q⁰-, in which R⁰ is hydrogen or methyl and Q⁰ is a direct bond; R³ ishydrogen R⁴ is methyl, fluoro, chloro, methoxy, or NO₂; I is 0 or 1; R⁵is H; Q is NR*; R* is H or methyl W is oxygen; V is N; X, Yindependently of one another are chloro, methyl, or methoxy; and Z isCH.